Caprolactam → hexanoic acid, 6-amino-, monosodium salt

HRID 275501

Reaction equation

[C:1]1(=[O:8])[NH:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)CCCCC(Cl)=[O:15].[OH-].[Na+:20]>>[NH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O-:8])=[O:15].[Na+:20]

Participants

Reactant 3

HCID 7768Caprolactam

HCID 14798Sodium Hydroxide

HCID 61034Adipoyl chloride

Product 1

HCID 23663648hexanoic acid, 6-amino-, monosodium saltYield 70%

Procedure

The literature has described various methods for preparation of TOCAP and related compounds. German Patent 949,568 (Kruckenberg) discloses the reaction of caprolactam with various acyl halides including adipoyl dichloride in the presence of sodium hydroxide. Once sodium 6-aminocaproate has formed, the reactor is charged with a first portion acyl halide, sodium hydroxide and then a final portion acyl halide. A related method is reported by Zinner et al in J. Prakt. Chem. 17, 147-153 (1962). The procedure requires the addition of all the sodium hydroxide to be charged to the reaction vessel at the beginning of the synthesis. The reported yield is 70% of theory.

Workup

customfor preparation of TOCAP

Sources & evidence

ORD record: ord-316f4a5c879942108f6bfa368ea58fce
Source dataset: uspto-grants-1995_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05393902

Linked notes

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