N-Methylbenzylamine → HCID 68619645, compound

HRID 1159366Notes

Reaction equation

HRID 1159366 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.[CH3:21][NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1>[CH2:23]([N:22]([CH3:21])[C:18]([CH:16]1[CH2:15][C:14](=[O:13])[CH2:17]1)=[O:20])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7669N-MethylbenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 49133583-Oxocyclobutane-1-carboxylic acid

Product 1

HCID 68619645HCID 68619645, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

CDI (40 g, 0.25 mol) was added to a solution of 3-oxo-cyclobutanecarboxylic acid (23 g, 0.2 mol) in THF (100 ml) at 0° C. under stirring, the mixture was stirred at RT for 1 h. N-methylbenzylamine (32 ml, 0.25 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, 500 g, CHCl3/MeOH 100:0→95:5). The title compound (27.9 g, 64%) was obtained as a colorless oil. 1H NMR data (DMSO-d6): 7.20 (m, 5H, Ph); 4.62 s, 4.55 s (2H, CH2); 3.46-3.62 (m, 1H); 3.28 (m, 4H,); 2.85 s, 2.94 s (3H, NCH3).

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, 500 g, CHCl3/MeOH 100:0→95:5)

Sources & evidence

ORD record
ord-9a02268c1c924d458a2d06ced58c6d2b
Source dataset
uspto-grants-2010_10
Patent number
US07812040B2

Reaction notes

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