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1-Methanesulphonyloxy-3-(3,4-dichlorophenyl)-4-[2-(2-methoxybenzoyl)imidazol-1-yl]butane → 4-Cyclohexyl-1-(3-[3,4-dichlorophenyl]-4-[2-(2-methoxybenzoyl)imidazol-1-yl]butyl)quinuclidinium methanesulphonate

HRID 1533023
Notes
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Reaction equation

HRID 1533023 reaction equation
[CH3:1][S:2]([O:5][CH2:6][CH2:7][CH:8]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=1)[CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[C:15](=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])(=[O:4])=[O:3].[CH:33]1([C:39]23[CH2:46][CH2:45][N:42]([CH2:43][CH2:44]2)[CH2:41][CH2:40]3)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>C(#N)C>[CH3:1][S:2]([O-:5])(=[O:4])=[O:3].[CH:33]1([C:39]23[CH2:46][CH2:45][N+:42]([CH2:6][CH2:7][CH:8]([C:25]4[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=4)[CH2:9][N:10]4[CH:14]=[CH:13][N:12]=[C:11]4[C:15](=[O:24])[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[O:22][CH3:23])([CH2:41][CH2:40]2)[CH2:43][CH2:44]3)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 226138281-Methanesulphonyloxy-3-(3,4-dichlorophenyl)-4-[2-(2-methoxybenzoyl)imidazol-1-yl]butaneHCID 226138404-Cyclohexylquinuclidine

Product 1

HCID 226138324-Cyclohexyl-1-(3-[3,4-dichlorophenyl]-4-[2-(2-methoxybenzoyl)imidazol-1-yl]butyl)quinuclidinium methanesulphonateYield 84.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Methanesulphonyloxy-3-(3,4-dichlorophenyl)-4-[2-(2-methoxybenzoyl)imidazol-1-yl]butane (0.59 g) (see Preparation 84) and 4-cyclohexylquinuclidine (0.27 g) (see Preparation 1) were dissolved in acetonitrile (8 ml) and heated under reflux for 3.5 hours. The solvent was removed under reduced pressure and the resulting residue dissolved in dichloromethane and the solvent removed under reduced pressure. The residue was chromatographed on silica gel eluting with a solvent gradient of 95:5 changing to 85:15, by volume, dichloromethane:methanol to give 4-cyclohexy-1-(3-[3,4-dichlorophenyl]-4-[2-(2-methoxybenzoyl)imidazol-1-yl]butyl)quinuclidinium methanesulphonate (0.69 g) as a white foam.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3.5 hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe resulting residue dissolved in dichloromethane
  5. customthe solvent removed under reduced pressure
  6. customThe residue was chromatographed on silica gel eluting with a solvent gradient of 95:5 changing to 85:15, by volume, dichloromethane

Sources & evidence

ORD record
ord-5737cbff146c417c9cdbfff80315a71c
Source dataset
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06207678B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes