Benzylamine → N-Benzyl-3-oxocyclobutanecarboxamide

HRID 1159360Notes

Reaction equation

HRID 1159360 reaction equation
[O:1]=[C:2]1[CH2:5][CH:4]([C:6]([OH:8])=O)[CH2:3]1.[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[CH2:9]([NH:16][C:6]([CH:4]1[CH2:3][C:2](=[O:1])[CH2:5]1)=[O:8])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 49133583-Oxocyclobutane-1-carboxylic acid

Product 1

HCID 68619384N-Benzyl-3-oxocyclobutanecarboxamideYield 40.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Acid, 3-oxocyclobutanecarboxylic acid (10 g, 0.087 mol), benzylamine (10.5 mL, 0.96 mol), and triethylamine (38 mL, 0.26 mol) were dissolved in DMF (100 mL). BOP (38.7 g, 0.087 mol) was added at 0° C. under stirring in argon. The mixture was stirred at 20° C. for 20 h, evaporated, and the residue was dried at 0.5 mmHg. The residue was purified by chromatography (silica gel, 63-100 μm, 1 L, CCl4→CHCl3, CHCl3/MeOH 100:0→95:5). The title compound (7.12 g, 40%) was obtained as a colorless oil. 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 20° C. for 20 h
  2. customevaporated
  3. customthe residue was dried at 0.5 mmHg
  4. customThe residue was purified by chromatography (silica gel, 63-100 μm, 1 L, CCl4→CHCl3, CHCl3/MeOH 100:0→95:5)

Sources & evidence

ORD record
ord-cc1fd52691344795ac6bf160c03d68bb
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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