Acetyl chloride → Tert-butyl 4-acetylpiperazine-1-carboxylate

HRID 1739749Notes

Reaction equation

HRID 1739749 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:21](Cl)(=[O:23])[CH3:22]>ClCCl>[C:21]([N:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 22707023Tert-butyl 4-acetylpiperazine-1-carboxylateYield 3.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-t-butoxycarbonylpiperazine (7 g, 1 mol. equiv.) in dichloromethane (140 ml) at 0° C. under nitrogen was added triethylamine (6.29 ml, 1.2 mol. equiv.). The reaction mixture was vigorously stirred and acetyl chloride (3.21 ml, 1.2 mol. equiv.) was added, dropwise. The mixture was stirred for twenty four hours. The reaction mixture was washed with saturated aqueous sodium bicarbonate solution (30 ml), and the organic layer dried using magnesium sulphate. The organic solvent was removed under reduced pressure and the residue purified by flash column chromatography on silica gel eluting with methanol:ethyl acetate (1:19, by volume) to give the title compound (8.19 g). TLC Rf=0.33 (silica, methanol:ethyl acetate, 1:19, by volume). LRMS m/z=229(m+1)+. Found: C, 57.83; H, 8.83; N, 12.27. C11H20N2O3 requires C, 57.87; H, 8.92; N, 12.14%.

Workup

  1. stirringThe mixture was stirred for twenty four hours
  2. washThe reaction mixture was washed with saturated aqueous sodium bicarbonate solution (30 ml)
  3. customthe organic layer dried
  4. customThe organic solvent was removed under reduced pressure
  5. customthe residue purified by flash column chromatography on silica gel eluting with methanol:ethyl acetate (1:19, by volume)

Sources & evidence

ORD record
ord-d1bd4a63687440a1b3be5789c3160196
Source dataset
uspto-grants-1999_10
Patent number
US05968923

Reaction notes

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