Sodium Chloride → 1-Methyl-3-phenyl-4-[2-hydroxy-2-(4-chlorophenyl)ethyl]piperazine

HRID 622780Notes

Reaction equation

HRID 622780 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[O:10])[CH:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:3]1.[BH4-].[Na+].[Cl-].[Na+]>C(O)C>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]([OH:10])[C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH:4]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:3]1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 143023441-Methyl-3-phenyl-4-(4-chlorophenacyl) piperazine

Product 1

HCID 143023451-Methyl-3-phenyl-4-[2-hydroxy-2-(4-chlorophenyl)ethyl]piperazineYield 63.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 25 g (0.076 mol) of the 1-methyl-3-phenyl-4-(4-chlorophenacyl) piperazine in 450 ml of ethanol was added in portions 2.9 (0.076 mol) of sodium borohydride. The resulting mixture was stirred at ambient temperature for 2 hours, poured into 50% aqueous sodium chloride and extracted with ethyl acetate. The organic extracts were combined, washed with water and saturated sodium chloride and dried over sodium sulfate. The resulting crude product obtained from concentration of the filtrate was subjected to rapid liquid chromatography on a silica gel column to give 16 g (60% overall) of 1-methyl-3-phenyl-4-[2-hydroxy-2-(4-chlorophenyl)ethyl]piperazine as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water and saturated sodium chloride
  3. dry with materialdried over sodium sulfate
  4. customThe resulting crude product obtained from concentration of the filtrate

Sources & evidence

ORD record
ord-e40b2381a4784ae5a95a81524de7bbc1
Source dataset
uspto-grants-1988_09
Patent number
US04772705

Reaction notes

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