Water → HCID 14551562, compound

HRID 1607903Notes

Reaction equation

HRID 1607903 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][C:21]4[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=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][C:21]4[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=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 14551561HCID 14551561, compound

Product 1

HCID 14551562HCID 14551562, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of [4-(1H-imidazol-1-yl)phenyl][1-(4-pyridylmethyl)-4-piperidinyl]methanone (5.70 g, 16.5 mmol) in methanol (100 ml) at 0° C. was added sodium borohydride (2.1 g, 56 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 three times 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 the desired product, α-[4-(1H-imidazol-1-yl)phenyl]-1-(4-pyridylmethyl)-4-piperidine methanol (2.5 g, 43%): m.p. 174°-175° C.

Workup

  1. concentrationthe solution was concentrated to a white suspension
  2. extractionThis aqueous suspension was extracted three times 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-20aa6ea639044b01bd11b46626f4256d
Source dataset
uspto-grants-1989_09
Patent number
US04868194

Reaction notes

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