Methanol → N-phenylcyclopropanecarboxamide

HRID 1839204Notes

Reaction equation

HRID 1839204 reaction equation
[C:1]1(CC=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15]C=CC=1.C[OH:19]>[Pd]>[C:1]1([NH:17][C:10]([CH:11]2[CH2:16][CH2:15]2)=[O:19])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 998PhenylacetaldehydeHCID 7504Benzylamine

Product 1

HCID 528617N-phenylcyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Phenylacetaldehyde (0.091 mL, 0.780 mmol) was added to N-benzylamine 86 (0.055 g, 0.156 mmol) dissolved in MeOH (5.2mL, 0.03M). 10% Pd/C (0.0557 g) was added, and the mixture was shaken under 40 psi H2 until the consumption of H2 ceased and the reaction was judged complete by TLC. The crude reaction mixture was passed through a column of Celite, concentrated in vacuo, and purified by flash column chromatography (50:48:2::Hexanes:CH2Cl2:2N NH3 in EtOH) to obtain pure 4-phenethyl-1,4-ozazepan-2-ylmethyl)-N-phenylcyclopropanamide (87). 1H NMR (CDCl3) 7.47 (2H, m), 7.37-7.26 (5H, m), 7.24-7.17 (3H, m), 3.94-3.80 (3H, m), 3.69 (1H, broad dd, J=13.3, 7.8 Hz), 3.62 (1H, ddd, J=11.7, 6.2, 5.3 Hz), 2.96-2.86 (2H, m), 2.77 (4H, s), 2.67 (1H, ddd, J=12.8, 8.9, 4.1 Hz), 2.50 (1H, dd, J=8.9, 6.7 Hz) 2.0-1.74 (2H, m), 1.42-1.28 (1H, m), 1.04 (2H, dtd, J=7.8, 3.4, 1.1 Hz), 0.67-0.60 (2H, m) ppm. 13C NMR (CDCl3) 173.79, 143.39, 140.46, 129.52, 128.82, 128.61, 128.44, 127.53, 126.05, 76.41, 67.15, 60.06, 59.53, 53.90, 52.09, 34.21, 30.28, 12.92, 8.71, 8.50 ppm. LRMS: 378.80.

Workup

  1. customThe crude reaction mixture
  2. concentrationconcentrated in vacuo
  3. custompurified by flash column chromatography (50:48:2::Hexanes:CH2Cl2:2N NH3 in EtOH)

Sources & evidence

ORD record
ord-3d12c9c29bcc4e29af90b915edddb302
Source dataset
uspto-grants-2004_01
Patent number
US06677332B1

Reaction notes

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