Sodium hydride → HCID 86755702, compound

HRID 1872771Notes

Reaction equation

HRID 1872771 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([CH3:24])[CH:23]=1)[C:5]([N:7]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9][C@@H:8]1[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:6].[H-].[Na+].Cl[C:28]1[N:32]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)[C:31]2[CH:41]=[CH:42][CH:43]=[CH:44][C:30]=2[N:29]=1>CN(C)C=O>[CH3:24][C:22]1[CH:21]=[C:4]([CH:3]=[C:2]([CH3:1])[CH:23]=1)[C:5]([N:7]1[CH2:12][CH2:11][C@H:10]([O:13][C:28]2[N:32]([CH2:33][C:34]3[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=3)[C:31]3[CH:41]=[CH:42][CH:43]=[CH:44][C:30]=3[N:29]=2)[CH2:9][C@@H:8]1[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 30202411-(4-Fluorobenzyl)-2-chlorobenzimidazoleHCID 86755703HCID 86755703, compound

Product 1

HCID 86755702HCID 86755702, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(±)-cis-1-(3,5-dimethylbenzoyl)-2-(phenylmethyl)-4-piperidinol (2.6 g) dissolved in N,N-dimethylformamide (100 ml) was stirred under N2. Sodium hydride (60%) (0.36 g) was added and the mixture was stirred at 40° C. for 1 hour. 2-Chloro-1-[(4-fluorophenyl)-methyl]-1H-benzimidazole (2.6 g) was added and the mixture was stirred at 60° C. for 20 hours. The solvent was evaporated and the residue was taken up in water and CH2Cl2. The organic layer was separated, dried, filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 97/3). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from DIPE, yielding 2.85 g (65%) of (±)-cis-1-(3,5-dimethylbenzoyl)-4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]oxy]-2-(phenylmethyl)piperidine (comp. 70; mp. 154.1° C.).

Workup

  1. stirringthe mixture was stirred at 40° C. for 1 hour
  2. stirringthe mixture was stirred at 60° C. for 20 hours
  3. customThe solvent was evaporated
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH 97/3)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. customThe residue was crystallized from DIPE

Sources & evidence

ORD record
ord-2a7033ef1ae645f1939f401c8072917a
Source dataset
uspto-grants-2000_08
Patent number
US06110939

Reaction notes

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