A mixture of 5-phthalimidopentyl bromide (Drake and Garman, J.Amer. Chem.
Sec, 1949, 71, 2426) (296.0 g) and potassium p-nitrophenoxide (177.0 g) in
ethanol (1.5 L) was stirred mechanically, boiled under reflux for 20 h,
concentrated to half its volume, cooled and filtered. The product was washed
with water, dried and crystallised from acetone, giving 1-p-nitrophenoxy-5-
phthalimidopentane, melting point 123°-124°C.
The foregoing 1-p-nitrophenoxy-5-phthalimidopentane (100.0 g) in ethanol (1
L) was reduced by hydrogen over 2% of platinum oxide at 74°C/73 lb. per sq.
in. The filtered solution on cooling gave L-p-aminophenoxy-5-phthalimidopentane, melting point 111°-112° C (recrystallisation from
ethanol).
