Water → HCID 14551559, compound

HRID 1607902Notes

Reaction equation

HRID 1607902 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12]([CH:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=4)[CH2:16][CH2:15]3)=[O:13])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[BH4-].[Na+].O>CO>[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([CH:12]([CH:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[C:24]([O:30][CH3:31])[CH:23]=4)[CH2:16][CH2:15]3)[OH:13])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 14551558HCID 14551558, compound

Product 1

HCID 14551559HCID 14551559, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of [4-(1H-imidazol-1-yl)phenyl][1-[2-(3,4-dimethoxyphenyl)ethyl]-4-piperidinyl]methanone (5.90 g, 14.1 mmol) in methanol (100 ml) at 0° C. was added sodium borohydride (1.80 g, 47.6 g mmol) in three equal portions over a 24 hour period. Water was added and the solution was concentrated to a white suspension. This aqueous suspension was extracted twice with dichloromethane. The combined organic layers were dried (MgSO4), and filtered through a pad of silica gel (eluting with acetone). The eluent was concentrated and the resulting solid was recrystallized from tetrahydrofuran to afford α-[4-(1H-imidazol-1-yl)phenyl]-1-[2-(3,4-dimethoxyphenyl)ethyl]-4-piperidine methanol (2.9 g, 49%): m.p. 59°-60° C.

Workup

  1. concentrationthe solution was concentrated to a white suspension
  2. extractionThis aqueous suspension was extracted twice with dichloromethane
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered through a pad of silica gel (eluting with acetone)
  5. concentrationThe eluent was concentrated
  6. customthe resulting solid was recrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-f1aef0428e6f46a692f334ceb7d4ac97
Source dataset
uspto-grants-1989_09
Patent number
US04868194

Reaction notes

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