Methanol → N-phenylcyclopropanecarboxamide

HRID 479811Notes

Reaction equation

HRID 479811 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-8af2883a98f747d7a2808d167a46d714
Source dataset
uspto-grants-2003_11
Patent number
US06645980B1

Reaction notes

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