Borane → HCID 68761225, compound

Participants

Reaction Steps

To a solution of 4-[(2-nitrophenyl)acetyl]morpholine (10 g, 40 mmol) in THF (250 ml) was added borane. THF (1.0M, 60 ml, 60 mmol) and the mixture heated at reflux for 1 h. A further portion of borane. THF (1.0M, 80 ml, 80 mmol) was added and reflux continued for 1 h. The cooled reaction was quenched by addition of hydrochloric acid (concentrated, 8 ml) and left at room temperature for 18 h. The mixture was concentrated under vacuum, basified with aqueous sodium hydroxide (2N) and extracted with ether (3×100 ml). The combined extracts were dried (magnesium sulphate) and the solvent evaporated under vacuum to give a crude sample of 4-[(2-nitrophenyl)ethyl]morpholine (11.42 g), which was used without further purification. Microanalysis: calculated C 61.007, H 6.83, N 11.86; found C 62.38; H, 8.02; N, 9.54.

Provenance & Evidence