Water → 6-Bromo-N,N-diethylhexanamide

A solution of 6-bromohexanoyl chloride (100 g, 468 mmol) in 350 ml of tetrahydrofuran was poured into a solution of diethylamine (1.08 moles, 79 g, 112 ml) in 800 ml of rapidly stirring water. The mixture was then extracted with 2×200 ml of CH2C12 and the pooled extracts were washed with 250 ml of brine. Drying over Na2SO4 and concentration under reduced pressure afforded 111.6 g (446 mmol, 100% yield) of product as a pale yellow oil: 1H NMR (Me2SO-d6, 300 MHz) δ 3.5 (t, J=6.7 Hz, 2 H ), 3.2°-3.3 (m, 4 H ), 2.3 (t, J=7.5 Hz, 2 H ), 1.8 (m, 2 H ), 1.3-1.6 (m, 4 H ), 1.1 (t, J=7.1 Hz, 3 H ), 0.99 (t, J=7.0 Hz, 3 H ).

1. extractionThe mixture was then extracted with 2×200 ml of CH2C12
2. washthe pooled extracts were washed with 250 ml of brine
3. dry with materialDrying over Na2SO4 and concentration under reduced pressure

ORD record

ord-edd9d9e51af846ebbba78435d2ff8836

Source dataset

uspto-grants-1995_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05438064