Benzylamine → N-Benzyl-3-oxocyclobutanecarboxamide

HRID 1485112Notes

Reaction equation

HRID 1485112 reaction equation
[O:1]=[C:2]1[CH2:5][CH:4]([C:6]([OH:8])=O)[CH2:3]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1>[CH2:21]([NH:28][C:6]([CH:4]1[CH2:3][C:2](=[O:1])[CH2:5]1)=[O:8])[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-oxocyclobutanecarboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-oxocyclobutanecarboxylic acid (13.5 g) in tetrahydrofuran (135 mL), 1,1′-carbonyldiimidazole (23.0 g) was added under cooling with ice. The mixture was brought to room temperature and stirred for 90 minutes. Benzylamine (15.5 mL) was added and the mixture was stirred at that temperature for 14 hours. The crude product was adsorbed on diatomaceous earth with the solvent being distilled off under reduced pressure. The crude product adsorbed on the diatomaceous earth was purified by silica gel column chromatography (chloroform:methanol=100:0-95:5) to give N-benzyl-3-oxocyclobutanecarboxamide as a colorless solid (16.9 g).

Workup

  1. temperatureunder cooling with ice
  2. customwas brought to room temperature
  3. stirringthe mixture was stirred at that temperature for 14 hours
  4. distillationbeing distilled off under reduced pressure
  5. customwas purified by silica gel column chromatography (chloroform:methanol=100:0-95:5)

Sources & evidence

ORD record
ord-ee4ffaf2e0a444609a475c70c1cd5aa5
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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