4-Bromobenzoic acid → N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-4-bromobenzamide

HRID 1726335노트

반응식

HRID 1726335 반응식
Cl.Cl.[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[C@@H:5]([NH2:11])[CH2:4]2.[Br:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=1>>[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[C@@H:5]([NH:11][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:13]([Br:12])=[CH:14][CH:15]=1)[CH2:4]2

참가 물질

3

반응물 2

HCID 114644-Bromobenzoic acidHCID 12494972(R)-(+)-3-Aminoquinuclidine Dihydrochloride

생성물 1

HCID 11461014N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-4-bromobenzamide

실험 절차

Prepared by a method analogous to that described for the preparation of Intermediate 1 from (R)-1-azabicyclo[2.2.2]oct-3-ylamine dihydrochloride and 4-bromobenzoic acid; the compound was purified by chromatography on silica gel using ammoniated methanol/chloroform mixtures as the eluent. The compound was then dissolved in tetrahydrofuran, excess hydrogen chloride (1M solution in diethyl ether) was added, and the solution was evaporated and then recrystallised from methanol/t-butyl methyl ether to give the hydrochloride salt of the title compound as a colourless solid; MS (ES+) 309, 311 (MH+).

후처리

  1. customPrepared by a method analogous to
  2. customthe compound was purified by chromatography on silica gel using ammoniated methanol/chloroform mixtures as the eluent
  3. dissolutionThe compound was then dissolved in tetrahydrofuran
  4. additionexcess hydrogen chloride (1M solution in diethyl ether) was added
  5. customthe solution was evaporated
  6. customrecrystallised from methanol/t-butyl methyl ether

출처 및 근거

ORD 기록
ord-c391c69198404aafa389b5b97a743a09
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07491734B2

반응 노트

불러오는 중…