Methanol → (S)-1-Acetyl-2-methyl-4-benzylpiperazine

HRID 1596216Notes

Reaction equation

HRID 1596216 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][C@@H:10]([CH3:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:22](OC(=O)C)(=[O:24])[CH3:23].CO>ClCCl>[C:22]([N:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][C@@H:10]1[CH3:14])(=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 6923224(S)-1-Benzyl-3-methylpiperazine

Product 1

HCID 54471759(S)-1-Acetyl-2-methyl-4-benzylpiperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (S)-1-benzyl-3-methylpiperazine (588 mg) and triethylamine (0.47 ml) in dichloromethane (5 ml) was added acetic anhydride (0.32 ml) at 0° C. The reaction mixture was stirred at ambient temperature for 4 hours. Methanol was added to this solution and evaporated. The residue was taken up in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by column chromatography eluting with a mixture of ethyl acetate and n-hexane (2:1) to give (S)-1-acetyl-4-benzyl-2-methylpiperazine (660 mg).

Workup

  1. customevaporated
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography
  6. washeluting with a mixture of ethyl acetate and n-hexane (2:1)

Sources & evidence

ORD record
ord-a5f6a829e6e14ff0b8e2c97bc765dc5d
Source dataset
uspto-grants-2001_09
Patent number
US06291464B1

Reaction notes

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