6-Methylpiperidin-2-one → 5-Aminohexanoic acid

Reaction equation

O[N:2]1[CH:7]([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]1=[O:9].[H][H].CC1NC(=[O:19])CCC1>[Pd]>[NH2:2][CH:7]([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]([OH:9])=[O:19]

Participants

Procedure

5-Aminohexanoic Acid was prepared by combining 0.5 g 2-methylcyclopentanone and 9.5 ml 2 N NaOH in sufficient ethanol to give a homogeneous solution. The mixture was cooled to 0° C., 0.9 g of benzene sulfohydroxamic acid (C6H5SO2NHOH) was added, and the mixture stored overnight in the refrigerator. Thereafter the mixture was concentrated in vacuo and extracted with ether. The post-extraction residue is brought to between pH 5-6 with 2 N HCl and extracted with chloroform to give an oil bp. 70°-80° C. (4 mm), 7-8% yield. This product N-hydroxy-6-methyl-2-piperidone, is reduced with hydrogen over 10% palladium-charcoal to a lactam, 6-methyl-2-piperidone (mp. 79°-80° C.). The lactam is hydrolyzed with aqueous Ba(OH)2 to yield 5-amino-hexanoic acid. ##STR7##