Sodium Hydroxide → 2H-Azepin-2-one, 3-aminohexahydro-

HRID 1011858Notes

Reaction equation

HRID 1011858 reaction equation
Cl.[NH2:2][C@H:3]([C:9]([OH:11])=O)[CH2:4][CH2:5][CH2:6][CH2:7][NH2:8].[OH-].[Na+]>C(O)CCC>[NH2:2][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1=[O:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69568L-Lysine monohydrochloride

Product 1

HCID 1024632H-Azepin-2-one, 3-aminohexahydro-

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
117 °C

Procedure

30 mmols of L-lysine hydrochloride 1 is neutralized with 30 mmols of NaOH and then 270 mmols of Al2O3 is added, followed by the addition of 120 ml of 1-butanol. This mixture is heated to 117° C. and is refluxed for six hours. The yield of α-amino-ε-caprolactam 2 produced by this reaction is about 92%.

Workup

  1. temperatureis refluxed for six hours

Sources & evidence

ORD record
ord-c5df58dac5ad42e6ab7bf7bdd02256e9
Source dataset
uspto-grants-2011_07
Patent number
US07977450B2

Reaction notes

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