Triethylamine → Tert-butyl 4-(4-amino-3-fluorobenzoyl)piperazine-1-carboxylate

HRID 1807719Notes

Reaction equation

HRID 1807719 reaction equation
CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O.[NH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([OH:26])=O)=[CH:22][C:21]=1[F:29].[N:30]1([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.C(N(CC)CC)C>ClCCl>[NH2:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([N:33]2[CH2:32][CH2:31][N:30]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:35][CH2:34]2)=[O:26])=[CH:22][C:21]=1[F:29]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 99714-Amino-3-fluorobenzoic acidHCID 111923Propylphosphonic anhydrideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 58055815Tert-butyl 4-(4-amino-3-fluorobenzoyl)piperazine-1-carboxylateYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Propanephosphonic acid cyclic anhydride (9.67 mmol, 5.76 mL, 50% solution in ethyl acetate) was added to a solution of 4-amino-3-fluorobenzoic acid (6.45 mmol, 1 g), tert-butyl piperazine-1-carboxylate (6.45 mmol, 1.2 g) and triethylamine (12.89 mmol, 1.74 mL) in dichloromethane (20 mL) and stirred for 2 hours. The reaction mixture was washed with sodium bicarbonate solution and concentrated under vacuum to give the title compound (2.09 g). MS (ESI) m/z 324.5 [M+H]+

Workup

  1. washThe reaction mixture was washed with sodium bicarbonate solution
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a04ca698404e48ce81d5c148e093f2c4
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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