Benzylamine → HCID 54041249, compound

Participants

Reaction Steps

A stirred solution of atropic acid (10.3 g, 69.5 mmol) in dry tetrahydrofuran (100 ml) was treated under nitrogen with N-methylmorpholine (7.7 ml, 70.0 mmol), cooled to -10°, treated dropwise with iso-butylchloroformate (9 ml, 69.4 mmol), treated dropwise with benzylamine (7.6 ml, 69.6 mmol), warmed to room temperature over 1 hour, filtered and evaporated in vacuo to give a yellow oil which was dissolved in ether (100 ml). The solution was washed with 0.1N-HCl (200 ml) , brine (100 ml), 0.1N-NaOH (100 ml) and brine (100 ml) , dried (MgSO4), and evaporated in vacuo to give a yellow liquid. Purification by chromatography (silica; di-iso-propyl ether) gave the product as white crystals (7.3 g), m.p. 84°-86° (from di-iso-propyl ether). (Found: C, 80.8; H, 6.3; N, 5.7. C16H15NO requires C, 81.0; H, 6.4; N, 5.9%.)

Provenance & Evidence