4-Phenyl-1-azabicyclo(2.2.2)octane → 4-Phenyl-1-(3-[3,4-dichlorophenyl]-4-{2-[3,5-bis(trifluoromethyl)benzoyl]imidazol-1-yl}butyl)quinuclidinium chloride

HRID 844540ノート

反応式

HRID 844540 の反応式
CS(O[CH2:6][CH2:7][CH:8]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=1)[CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[C:15](=[O:30])[C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=1)(=O)=O.[C:39]1([C:45]23[CH2:52][CH2:51][N:48]([CH2:49][CH2:50]2)[CH2:47][CH2:46]3)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(#N)C>[Cl-:37].[C:39]1([C:45]23[CH2:52][CH2:51][N+:48]([CH2:6][CH2:7][CH:8]([C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=4)[CH2:9][N:10]4[CH:14]=[CH:13][N:12]=[C:11]4[C:15](=[O:30])[C:16]4[CH:17]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:19]=[C:20]([C:22]([F:24])([F:23])[F:25])[CH:21]=4)([CH2:47][CH2:46]2)[CH2:49][CH2:50]3)[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

参加物

4

反応物 2

HCID 1428104-Phenyl-1-azabicyclo(2.2.2)octaneHCID 226138441-Methanesulphonyloxy-3-(3,4-dichlorophenyl)-4-{2-[3,5-bis(trifluoromethyl)benzoyl]imidazol-1-yl}butane

生成物 1

HCID 226138184-Phenyl-1-(3-[3,4-dichlorophenyl]-4-{2-[3,5-bis(trifluoromethyl)benzoyl]imidazol-1-yl}butyl)quinuclidinium chloride収率 87.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

1-Methanesulphonyloxy-3-(3,4-dichlorophenyl)-4-{2-[3,5-bis(trifluoromethyl)benzoyl]imidazol-1-yl}butane (0.7 g) (see Preparation 85) and 4-phenylquinuclidine (0.32 g) (see J. Org. Chem., 22, 1484,(1957)) were dissolved in acetonitrile (10 ml) and the mixture heated under reflux for 18 hours. The solvent was removed under reduced pressure and the resulting residue dissolved in dichloromethane and washed twice with 2N aqueous hydrochloric acid solution. The organic phase was then dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to give a residue which was chromatographed on silica gel eluting with a solvent gradient of 95:5 changing to 90:10, by volume, dichloromethane:methanol to give 4-phenyl-1-(3-[3,4-dichlorophenyl]-4-{2-[3,5-bis(trifluoromethyl)benzoyl]imidazol-1-yl}butyl)quinuclidinium chloride (0.37 g) as a white foam.

後処理

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 18 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe resulting residue dissolved in dichloromethane
  5. washwashed twice with 2N aqueous hydrochloric acid solution
  6. dry with materialThe organic phase was then dried over anhydrous sodium sulphate
  7. customthe solvent removed under reduced pressure
  8. customto give a residue which
  9. customwas chromatographed on silica gel eluting with a solvent gradient of 95:5 changing to 90:10, by volume, dichloromethane

出典と根拠

ORDレコード
ord-e85a767ebb13487bbf282110e4aa2643
出典データセット
uspto-grants-2002_04
特許番号
US06380396B1

反応ノート

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