4-Aminobenzoic Acid → Tert-butyl 4-(4-aminobenzoyl)piperazine-1-carboxylate

HRID 1807712Notes

Reaction equation

HRID 1807712 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][CH:21]=1.[N:29]1([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C(N(CC)CC)C>ClCCl>[NH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([N:32]2[CH2:31][CH2:30][N:29]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:34][CH2:33]2)=[O:26])=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 9784-Aminobenzoic AcidHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 2763355Tert-butyl 4-(4-aminobenzoyl)piperazine-1-carboxylateYield 68.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Propanephosphonic acid cyclic anhydride (10.94 mmol, 6.51 mL, 6.96 g, 50% solution in ethyl acetate) was added to a stirred solution of 4-aminobenzoic acid (7.29 mmol, 1 g), tert-butyl piperazine-1-carboxylate (7.29 mmol, 1.358 g) and triethylamine (14.58 mmol, 1.969 mL, 1.473 g) in dichloromethane (30 mL). The reaction mixture was stirred for 5 hours, then was washed with sodium bicarbonate and filtered through silica, eluting with ethyl acetate. Evaporation of solvent afforded the title compound (1.53 g). 1H NMR (MeOD, 400 MHz): δ 1.4 (9H, s), 3.4 (4H, m), 3.6 (4H, m), 6.7 (1H, m), 7.2 (2H, m)

Workup

  1. washwas washed with sodium bicarbonate
  2. filtrationfiltered through silica
  3. washeluting with ethyl acetate
  4. customEvaporation of solvent

Sources & evidence

ORD record
ord-4f02581d2f1440ca85234b2e32d07d33
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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