2-Methylcyclopentanone → 5-Aminohexanoic acid
Reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH2:4][C:3]1=[O:7].[OH-:8].[Na+].C1C=CC(S(O)(=O)=[N:17]O)=CC=1>C(O)C>[NH2:17][CH:2]([CH3:1])[CH2:6][CH2:5][CH2:4][C:3]([OH:7])=[O:8]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
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 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##
Workup
- customto give a homogeneous solution
- concentrationThereafter the mixture was concentrated in vacuo
- extractionextracted with ether
- extractionextracted with chloroform
Sources & evidence
- ORD record
- ord-a5bda7a748034c6b877de8eba9a8aab2
- Source dataset
- uspto-grants-1983_02
- Patent number
- US04372974
Reaction notes
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