Methanol → HCID 21545573, compound

HRID 1605922Notes

Reaction equation

HRID 1605922 reaction equation
[O:1]=[C:2]([CH2:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[CH2:3][N:4]1[CH2:9][CH2:8][C:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)([OH:10])[CH2:6][CH2:5]1.[BH4-].[Na+].CO>O>[OH:1][CH:2]([CH2:18][O:19][C:20]1[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=1)[CH2:3][N:4]1[CH2:9][CH2:8][C:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)([OH:10])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 21545591HCID 21545591, compound

Product 1

HCID 21545573HCID 21545573, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.9 g of 1-[2-oxo-3-(p-fluorophenoxy)propyl]-4-(p-chlorophenyl)-4-hydroxypiperidine, 0.38 g of sodium borohydride and 20 ml of methanol is stirred at room temperature for 3 hours. The resulting mixture is diluted with water and extracted with chloroform. The organic layer is dried over sodium sulfate and evaporated under reduced pressure to give 1-[2-hydroxy-3-(p-fluorophenoxy)propyl]-4-(p-chlorophenyl)-4-hydroxypiperidine, M.P. 103° to 105°C. Recrystallization from benzene-cyclohexane gives white crystals, M.P. 107° to 108°C.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer is dried over sodium sulfate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fe7959f5a99e4ee5aca15c9f07466440
Source dataset
uspto-grants-1976_04
Patent number
US03951986

Reaction notes

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