• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】14717

【品名】N-(2-fluorophenyl)-2-methoxy-N-(3-methyl-4-piperidinyl)acetamide

【CA登记号】

【 分 子 式 】C15H21FN2O2

【 分 子 量 】280.3424232

【元素组成】C 64.27% H 7.55% F 6.78% N 9.99% O 11.41%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(V)

Condensation of the piperidone (I) with 2-fluoroaniline (II), followed by reduction of the Schiff base with sodium borohydride afforded 1-benzyl-3-methyl-4-phenylaminopiperidine (III). Intermediate (III) was produced in an approximate 7:3 (cis/trans) isomeric ratio. Acylation of (III) with methoxyacetyl chloride gave compound (IV) and subsequent catalytic debenzylation gave the compound (V), which was N-alkylated in acetonitrile with 1-(2-bromoethyl)-4-ethyl-1,4-dihydro-5H-tetrazol-5-one (VI). Brifentanil is the cis-isomer obtained by the chromatographic separation of the isomeric mixture.

1 Huang, B.-S.; Deutsche, K.H.; Lalinde, N.L.; Terrell, R.C.; Kudzma, L.V. (BOC Health Care, Inc.); (BOC, Inc.). N-Aryl-N-(4-piperidinyl)amides and pharmaceutical compsns. and method employing such cpds. EP 0160422; ES 8609251; ES 8705387; JP 1985248670; US 4584303 .
2 Ossipov, M.H.; Wright, D.; Spencer, K.H.; Spaulding, T.C.; Lalinde, N.; Moliterni, J.; Rufo, F.G.; Synthesis and pharmacological evaluation of a series of new 3-methyl-1,4-disubstituted-piperidine analgesics. J Med Chem 1989, 33, 10, 2876-82.
3 Moliterni, J.; Spencer H.K.; Rudo, F.G.; Ossipov, M.H.; Spaulding, T.C.; Lalinde, N.; Wright, D.; Waters, S.J.; Brifentanil Hydrochloride. Drugs Fut 1991, 16, 8, 706.
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) 14714 1-Benzyl-3-methyl-4-piperidone; 1-benzyl-3-methyltetrahydro-4(1H)-pyridinone 34737-89-8 C13H17NO 详情 详情
(II) 22296 2-fluorophenylamine; 2-fluoroaniline 348-54-9 C6H6FN 详情 详情
(III) 14715 N-(1-benzyl-3-methyl-4-piperidinyl)-N-(2-fluorophenyl)amine; 1-benzyl-N-(2-fluorophenyl)-3-methyl-4-piperidinamine C19H23FN2 详情 详情
(IV) 14716 N-(1-benzyl-3-methyl-4-piperidinyl)-N-(2-fluorophenyl)-2-methoxyacetamide C22H27FN2O2 详情 详情
(V) 14717 N-(2-fluorophenyl)-2-methoxy-N-(3-methyl-4-piperidinyl)acetamide C15H21FN2O2 详情 详情
(VI) 14421 (2R,3S)-2,3-bis([[tert-butyl(dimethyl)silyl]oxy]methyl)cyclobutanone O-methyloxime C19H41NO3Si2 详情 详情
(VII) 14718 N-[1-[2-(4-ethyl-5-oxo-4,5-dihydro-1H-1,2,3,4-tetraazol-1-yl)ethyl]-3-methyl-4-piperidinyl]-N-(2-fluorophenyl)-2-methoxyacetamide C20H29FN6O3 详情 详情
Extended Information