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【结 构 式】 
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【分子编号】34744 【品名】1-[(2-chloroethoxy)(phenyl)methyl]benzene; benzhydryl 2-chloroethyl ether 【CA登记号】32669-06-0 |
【 分 子 式 】C15H15ClO 【 分 子 量 】246.7362 【元素组成】C 73.02% H 6.13% Cl 14.37% O 6.48% |
合成路线1
该中间体在本合成路线中的序号：(I)The title compound was obtained by two related procedures. Reaction of 4-piperidone-HCl (II) with 2-(benzhydryloxy)ethyl chloride (I) in the presence of Na2CO3 and NaI provided the N-alkylated piperidone (III). Horner-Emmons condensation of (III) with triethyl phosphonoacetate (IV) and NaH gave rise to the piperidylidene acetate (V). Then, hydrogenation of the double bond of (V) using Raney Nickel yielded the target compound.
| 【1】 Buzas, A.; Merour, J.-Y.; Ollivier, R. (Laboratoires Meram SA); Benzhydryloxyethylpiperidine derivs., process for their preparation and pharmaceutical compsns., in which they are present. EP 0259227; US 4983614 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 34744 | 1-[(2-chloroethoxy)(phenyl)methyl]benzene; benzhydryl 2-chloroethyl ether | 32669-06-0 | C15H15ClO | 详情 | 详情 |
| (II) | 27115 | 4-piperidinone | 40064-34-4 | C5H9NO | 详情 | 详情 |
| (III) | 34745 | 1-[2-(benzhydryloxy)ethyl]-4-piperidinone | C20H23NO2 | 详情 | 详情 | |
| (IV) | 10019 | Ethyl 2-(diethoxyphosphoryl)acetate; Triethyl phosphonoacetate | 867-13-0 | C8H17O5P | 详情 | 详情 |
| (V) | 34746 | ethyl 2-[1-[2-(benzhydryloxy)ethyl]-4-piperidinylidene]acetate | C24H29NO3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(I)Horner-Emmons condensation of 1-benzyl-4-piperidone (VI) with phosphonate (IV) furnished the unsaturated ester (VII). Hydrogenation of (VII) over Pd/C produced double bond reduction and simultaneous N-benzyl group cleavage to afford piperidine (VIII). This was finally alkylated with chloride (I) in the presence of K2CO3 and NaI.
| 【1】 Buzas, A.; Merour, J.-Y.; Ollivier, R. (Laboratoires Meram SA); Benzhydryloxyethylpiperidine derivs., process for their preparation and pharmaceutical compsns., in which they are present. EP 0259227; US 4983614 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 34744 | 1-[(2-chloroethoxy)(phenyl)methyl]benzene; benzhydryl 2-chloroethyl ether | 32669-06-0 | C15H15ClO | 详情 | 详情 |
| (IV) | 10019 | Ethyl 2-(diethoxyphosphoryl)acetate; Triethyl phosphonoacetate | 867-13-0 | C8H17O5P | 详情 | 详情 |
| (VI) | 15720 | 1-benzyltetrahydro-4(1H)-pyridinone; 1-Benzyl-4-piperidone; N-Benzyl-4-piperidone; 1-(benzyl)-4-piperidinone; 1-benzylpiperidin-4-one; 1-(benzyl)piperidin-4-one | 3612-20-2 | C12H15NO | 详情 | 详情 |
| (VII) | 34747 | ethyl 2-(1-benzyl-4-piperidinylidene)acetate | C16H21NO2 | 详情 | 详情 | |
| (VIII) | 28087 | 4-Piperidineacetic acid ethyl ester; ethyl 2-(4-piperidinyl)acetate | C9H17NO2 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(I)The title compound was obtained by two related procedures. Reaction of 4-piperidone-HCl (II) with 2-(benzhydryloxy)ethyl chloride (I) in the presence of Na2CO3 and NaI provided the N-alkylated piperidone (III). Horner-Emmons condensation of (III) with triethyl phosphonoacetate (IV) and NaH gave rise to the piperidylidene acetate (V). Then, hydrogenation of the double bond of (V) using Raney Nickel and hydrolysis yielded the target compound.
| 【1】 Buzas, A.; Merour, J.-Y.; Ollivier, R. (Laboratoires Meram SA); Benzhydryloxyethylpiperidine derivs., process for their preparation and pharmaceutical compsns., in which they are present. EP 0259227; US 4983614 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 34744 | 1-[(2-chloroethoxy)(phenyl)methyl]benzene; benzhydryl 2-chloroethyl ether | 32669-06-0 | C15H15ClO | 详情 | 详情 |
| (II) | 27115 | 4-piperidinone | 40064-34-4 | C5H9NO | 详情 | 详情 |
| (III) | 34745 | 1-[2-(benzhydryloxy)ethyl]-4-piperidinone | C20H23NO2 | 详情 | 详情 | |
| (IV) | 10019 | Ethyl 2-(diethoxyphosphoryl)acetate; Triethyl phosphonoacetate | 867-13-0 | C8H17O5P | 详情 | 详情 |
| (V) | 34746 | ethyl 2-[1-[2-(benzhydryloxy)ethyl]-4-piperidinylidene]acetate | C24H29NO3 | 详情 | 详情 | |
| (VI) | 34748 | ethyl 2-[1-[2-(benzhydryloxy)ethyl]-4-piperidinyl]acetate | C24H31NO3 | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(I)Horner-Emmons condensation of 1-benzyl-4-piperidone (VII) with phosphonate (IV) furnished the unsaturated ester (VIII). Hydrogenation of (VIII) over Pd/C produced double bond reduction and simultaneous N-benzyl group cleavage to afford piperidine (IX). This was finally alkylated with chloride (I) in the presence of K2CO3 and NaI and hydrolyzed to target compound.
| 【1】 Buzas, A.; Merour, J.-Y.; Ollivier, R. (Laboratoires Meram SA); Benzhydryloxyethylpiperidine derivs., process for their preparation and pharmaceutical compsns., in which they are present. EP 0259227; US 4983614 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 34744 | 1-[(2-chloroethoxy)(phenyl)methyl]benzene; benzhydryl 2-chloroethyl ether | 32669-06-0 | C15H15ClO | 详情 | 详情 |
| (IV) | 10019 | Ethyl 2-(diethoxyphosphoryl)acetate; Triethyl phosphonoacetate | 867-13-0 | C8H17O5P | 详情 | 详情 |
| (VI) | 34748 | ethyl 2-[1-[2-(benzhydryloxy)ethyl]-4-piperidinyl]acetate | C24H31NO3 | 详情 | 详情 | |
| (VII) | 15720 | 1-benzyltetrahydro-4(1H)-pyridinone; 1-Benzyl-4-piperidone; N-Benzyl-4-piperidone; 1-(benzyl)-4-piperidinone; 1-benzylpiperidin-4-one; 1-(benzyl)piperidin-4-one | 3612-20-2 | C12H15NO | 详情 | 详情 |
| (VIII) | 34747 | ethyl 2-(1-benzyl-4-piperidinylidene)acetate | C16H21NO2 | 详情 | 详情 | |
| (IX) | 28087 | 4-Piperidineacetic acid ethyl ester; ethyl 2-(4-piperidinyl)acetate | C9H17NO2 | 详情 | 详情 |