Sodium hydride → 1-(Cyclopropylmethyl)-6-phenylazepan-2-one

HRID 1725607Notes

Reaction equation

HRID 1725607 reaction equation
[H-].[Na+].[C:3]1([CH:9]2[CH2:15][NH:14][C:13](=[O:16])[CH2:12][CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:17]1([CH2:20]Br)[CH2:19][CH2:18]1>CN(C)C=O>[CH:17]1([CH2:20][N:14]2[CH2:15][CH:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:10][CH2:11][CH2:12][C:13]2=[O:16])[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 127649286-Phenylazepan-2-one

Product 1

HCID 184519061-(Cyclopropylmethyl)-6-phenylazepan-2-oneYield 72.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil; 0.793 g, 19.8 mmol) was added to a solution of 6-phenylazepan-2-one (2.50 g, 13.2 mmol) and cyclopropylmethyl bromide (1.92 mL, 19.8 mmol) in N,N-dimethylformamide (30 mL) at 0° C. and then warmed to ambient temperature. After 18 h the mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with water (3×) and saturated brine, dried over magnesium sulfate, filtered, and concentrated. Purification by silica gel chromatography (1% methanol/dichloromethane→5% methanol/dichloromethane) gave the title compound (2.33 g). MS 244 (M+1).

Workup

  1. customAfter 18 h the mixture was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water (3×) and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (1% methanol/dichloromethane→5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-c0475566c47f41028f0a18fc7365fc9c
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

Loading…