Sodium borohydride → N-(2,6-dimethylphenyl)-2-{4-[3-hydroxy-4-(2-methoxyphenyl)butyl]piperazin-1-yl}acetamide

HRID 230118Notes

Reaction equation

HRID 230118 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10](=[O:31])[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20](=[O:30])[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][CH3:29])[CH2:14][CH2:13]1.[BH4-].[Na+]>C(O)C>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[NH:9][C:10](=[O:31])[CH2:11][N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH:20]([OH:30])[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[O:28][CH3:29])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18452748N-(2,6-dimethylphenyl)-2-{4-[4-(2-methoxyphenyl)-3-oxobutyl]piperazin-1-yl}acetamide

Product 1

HCID 11743169N-(2,6-dimethylphenyl)-2-{4-[3-hydroxy-4-(2-methoxyphenyl)butyl]piperazin-1-yl}acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-(2,6-dimethylphenyl)-2-{4-[4-(2-methoxyphenyl)-3-oxobutyl]piperazin-1-yl}acetamide (100 mg, 0.23 mmol) in ethanol (2 mL) was added sodium borohydride (50 mg), and the mixture was stirred for 16 hours. Excess borohydride was then quenched by the addition of saturated ammonium chloride solution. Dichloromethane (20 mL) was added, the mixture shaken, and the organic layer was separated, washed with water and concentrated under reduced pressure. The residue obtained was purified by preparative TLC using 10% methanol in dichloromethane as mobile phase to afford N-(2,6-dimethylphenyl)-2-{4-[3-hydroxy-4-(2-methoxyphenyl)butyl]piperazin-1-yl}acetamide, a compound of Formula I.

Workup

  1. customExcess borohydride was then quenched by the addition of saturated ammonium chloride solution
  2. additionDichloromethane (20 mL) was added
  3. stirringthe mixture shaken
  4. customthe organic layer was separated
  5. washwashed with water
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-431eec975ac642738979725953056fca
Source dataset
uspto-grants-2009_07
Patent number
US07566717B2

Reaction notes

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