Acetyl chloride → (+/-)-1-BOC-4-acetyl-3-phenyl-piperazine

HRID 530626Notes

Reaction equation

HRID 530626 reaction equation
[C:1]1([CH:7]2[NH:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:27](Cl)(=[O:29])[CH3:28]>ClCCl.C(=O)(O)[O-].[Na+]>[C:16]([O:15][C:13]([N:9]1[CH2:10][CH2:11][N:12]([C:27](=[O:29])[CH3:28])[CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 2735358Tert-butyl 3-phenylpiperazine-1-carboxylate

Product 1

HCID 67083964(+/-)-1-BOC-4-acetyl-3-phenyl-piperazineYield 54%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of tert-butyl 3-phenylpiperazine-1-carboxylate (400 mg, 1.52 mmol) and triethyl amine (309 mg, 3.05 mmol) in dichloromethane (5 mL) was added acetyl chloride (156 mg, 1.98 mmol) at 0° C. After stirring for 3 h at room temperature, the reaction mixture was diluted with saturated sodium bicarbonate solution and dichloromethane. The aqueous part was extracted with dichloromethane and the combined organic part was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (20/1 dichloromethane/methanol) to afford 4-acetyl-3-phenyl-piperazine-1-carboxylic acid tert-butyl ester (250 mg, 54%). [M-BOC]H+=205.

Workup

  1. extractionThe aqueous part was extracted with dichloromethane
  2. dry with materialthe combined organic part was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (20/1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-5490e463d5c44e0786f3c839e3fc72c5
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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