Triethylamine → Tert-butyl 4-[2-(4-methylphenyl)-2-oxoethyl]piperazine-1-carboxylate

HRID 220835

Reaction equation

HRID 220835 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH2:10]Br)=[O:9])=[CH:4][CH:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C>ClCCl>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([CH2:10][C:8](=[O:9])[C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 692722-Bromo-4'-methylacetophenoneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 56771152Tert-butyl 4-[2-(4-methylphenyl)-2-oxoethyl]piperazine-1-carboxylateYield 77.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Bromo-4-methylacetophenone (572 mg, 2.68 mmol) was added to a solution of piperazine-1-carboxylic acid tert-butyl ester (500 mg, 2.68 mmol) in dichloromethane (5 ml) and triethylamine (0.45 ml, 3.22 mmol). The mixture was stirred for 3 days at room temperature and solvents were removed in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 40% hexane:60% EtOAc) to yield the title compound (661 mg, 77%).

Workup

  1. customsolvents were removed in vacuo
  2. customThe residue was purified by flash chromatography on silica gel (eluant; 40% hexane:60% EtOAc)

Sources & evidence

ORD record
ord-a9bb02082cad45c188aba1641b604799
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Linked notes

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