Acetic Anhydride → (S)-4-Acetyl-2-piperazinemethanol

HRID 1196874Notes

Reaction equation

HRID 1196874 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][C@H:2]1[CH2:7][OH:8].[C:9](OC(=O)C)(=[O:11])[CH3:10].C(=O)([O-])[O-].[Na+].[Na+]>O.C(N(CC)CC)C>[NH3:1].[C:9]([N:4]1[CH2:5][CH2:6][NH:1][C@H:2]([CH2:7][OH:8])[CH2:3]1)(=[O:11])[CH3:10]

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 14288866[(2S)-piperazin-2-yl]methanol

Product 2

HCID 222AmmoniaHCID 45086134(S)-4-Acetyl-2-piperazinemethanolYield 287.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Procedure

A solution of (S)-2-piperazinemethanol (1.25 g) in a mixture of water (12 ml) and triethylamine (3.2 ml) at ambient temperature was treated with a solution of acetic anhydride (1.25 ml; 1.32 mmol) in water (25 ml). The mixture was stirred at ambient temperature for 1 h, and anhydrous sodium carbonate (2 g) was added. The solvent was removed in vacuo. The residue was purified by flash column chromatography using dichloromethane:methanol:ammonia, 75:10:2 as eluant to give the title compound as a pale yellow oil (0.6 g).

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-87fb5d5dabe04b9784a6cdd10cc24fab
Source dataset
uspto-grants-1992_05
Patent number
US05116842

Reaction notes

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