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

HRID 1257108Notes

Reaction equation

HRID 1257108 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[C:21](Cl)(=[O:23])[CH3:22]>ClCCl>[C:21]([N:11]1[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]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 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-Boc-piperazine (300 mg, 1.63 mmol), triethylamine (494 mg, 3 equiv), and acetyl chloride (1.5 equiv) in dichloromethane was stirred overnight at rt. The solution was quenched by the dropwise addition of water. The organic layer was separated, dried over anhydrous Na2SO4, and evaporated in vacuo. The residue was purified by flash chromatography to give the title compound (˜85% yield) as a solid.

Workup

  1. customThe solution was quenched by the dropwise addition of water
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-17373938cac64b8cac4b38ed704fe09c
Source dataset
uspto-grants-2013_06
Patent number
US08461339B2

Reaction notes

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