ethyl 2-(1-benzyl-4-piperidinylidene)acetate -Drug Synthesis Database

【结构式】

【分子编号】34747

【品名】ethyl 2-(1-benzyl-4-piperidinylidene)acetate

【CA登记号】

【分子式】C₁₆H₂₁NO₂

【分子量】259.34828

【元素组成】C 74.1% H 8.16% N 5.4% O 12.34%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(VII)

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.

参考文献中间体

合成目标

【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2

该中间体在本合成路线中的序号：(VIII)

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.

参考文献中间体

合成目标

【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

Extended Information