Triethylamine → Tert-butyl 4-(2-(4-chlorophenoxy)acetyl)piperazine-1-carboxylate

HRID 718238Notes

Reaction equation

HRID 718238 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:21][C:22]1[CH:32]=[CH:31][C:25]([O:26][CH2:27][C:28](Cl)=[O:29])=[CH:24][CH:23]=1>ClCCl>[Cl:21][C:22]1[CH:32]=[CH:31][C:25]([O:26][CH2:27][C:28]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)=[O:29])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77771p-Chlorophenoxyacetyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 50941486Tert-butyl 4-(2-(4-chlorophenoxy)acetyl)piperazine-1-carboxylateYield 1,004%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl piperazine-1-carboxylate (0.30 g, 0.16 mmol) and triethylamine (0.34 ml, 2.42 mmol) in dichloromethane (8 ml) was added p-chlorophenoxyacetyl chloride (0.36 mg, 1.77 mmol). The reaction mixture was stirred at room temperature overnight. The mixture was diluted with dichloromethane and washed with water, brine and dried over Na2SO4. After removing the solvents, the crude residue was purified by chromatography on silica gel (CH2Cl2/MeOH 80:1) to yield the title compound as a white solid (0.57 g, 100%).

Workup

  1. washwashed with water, brine
  2. dry with materialdried over Na2SO4
  3. customAfter removing the solvents
  4. customthe crude residue was purified by chromatography on silica gel (CH2Cl2/MeOH 80:1)

Sources & evidence

ORD record
ord-05556084aedc4b13a3ceac79e50ba5cd
Source dataset
uspto-grants-2015_11
Patent number
US09193741B2

Reaction notes

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