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【结 构 式】

【药物名称】BM-212

【化学名称】1-[2-(Diphenylmethoxy)ethyl]piperidine-4-acetic acid

【CA登记号】

【 分 子 式 】C22H27NO3

【 分 子 量 】353.46539

【开发单位】Meram (Originator)

【药理作用】Antiallergy/Antiasthmatic Drugs, Asthma Therapy, RESPIRATORY DRUGS, Histamine H1 Antagonists

合成路线1

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2

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
Extended Information