Benzylamine → N-Benzyl-3-oxocyclobutanecarboxamide

HRID 1159389Notes

Reaction equation

HRID 1159389 reaction equation
C1N=CN(C(N2C=NC=C2)=O)C=1.[O:13]=[C:14]1[CH2:17][CH:16]([C:18]([OH:20])=O)[CH2:15]1.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH2:21]([NH:28][C:18]([CH:16]1[CH2:15][C:14](=[O:13])[CH2:17]1)=[O:20])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 49133583-Oxocyclobutane-1-carboxylic acid

Product 1

HCID 68619384N-Benzyl-3-oxocyclobutanecarboxamideYield 89.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

CDI (10.2 g, 0.063 mol) was added to a solution of 3-oxo-cyclobutanecarboxylic acid (6 g, 0.052 mol) in THF (60 ml) at 0° C. under stirring, the mixture was stirred at RT for 1 h. Benzylamine (6.9 ml, 0.063 mol) was added to the mixture and the mixture was stirred at RT for 3 h and evaporated. The residue was purified by chromatography (silica gel, 63-100 μm, 300 g, CHCl3/MeOH 100:0→95:5) to give the title compound (9.5 g, 89%) as white crystals. LC/MS data: 204.0, 205.1 (M+H) (calculated for C12H13NO2 203.24). 1H NMR data (DMSO-d6): 8.62 (br.s, 1H, NH); 7.21-7.36 (m, 5H, Ph); 4.32 (d, 2H, CH2, J=6.1 Hz); 3.10-3.28 (m, 5H).

Workup

  1. stirringthe mixture was stirred at RT for 1 h
  2. stirringthe mixture was stirred at RT for 3 h
  3. customevaporated
  4. customThe residue was purified by chromatography (silica gel, 63-100 μm, 300 g, CHCl3/MeOH 100:0→95:5)

Sources & evidence

ORD record
ord-8a662f1ed5a244229f7dc3ebc6c09585
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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