Sodium borohydride → N,N-Diethyl-2-[4-(2-fluoro-4-hydroxymethyl-phenyl)-piperazin-1-yl]-2-phenyl-acetamide

HRID 1927625Notes

Reaction equation

HRID 1927625 reaction equation
[CH2:1]([N:3]([CH2:28][CH3:29])[C:4](=[O:27])[CH:5]([N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]=[O:25])=[CH:20][C:19]=2[F:26])[CH2:14][CH2:13]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:2].[BH4-].[Na+]>C(O)C>[CH2:28]([N:3]([CH2:1][CH3:2])[C:4](=[O:27])[CH:5]([N:12]1[CH2:13][CH2:14][N:15]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][OH:25])=[CH:20][C:19]=2[F:26])[CH2:16][CH2:17]1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:29]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86612370N,N-Diethyl-2-[4-(2-fluoro-4-formyl-phenyl)-piperazin-1-yl]-2-phenyl-acetamide

Product 1

HCID 69304083N,N-Diethyl-2-[4-(2-fluoro-4-hydroxymethyl-phenyl)-piperazin-1-yl]-2-phenyl-acetamideYield 95.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N,N-diethyl-2-[4-(2-fluoro-4-formyl-phenyl)-piperazin-1-yl]-2-phenyl-acetamide (0.76 g, 1.92 mmol) in ethanol (35 mL) was treated with NaBH4 (0.11 g). After 3 d, the solvent was removed and water (5 mL) and 1 M NaOH were added (˜pH 10). The mixture was extracted with DCM and the solvent removed. Purification on SiO2EtOAc/hexanes) provided 0.73 g of the title compound. MS (ESI): mass calcd. for C23H30FN3O2, 399.5. m/z found, 400.5 [M+H]+.

Workup

  1. customthe solvent was removed
  2. additionwater (5 mL) and 1 M NaOH were added (˜pH 10)
  3. extractionThe mixture was extracted with DCM
  4. customthe solvent removed
  5. customPurification on SiO2EtOAc/hexanes)

Sources & evidence

ORD record
ord-32f58be973b34846b393b8fee3648af8
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

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