Propylene Glycol → 2H-Azepin-2-one, 3-aminohexahydro-

HRID 384617Notes

Reaction equation

HRID 384617 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)C(O)C>>[NH2:2][CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1=[O:11]

Participants

4

Reactant 3

HCID 1030Propylene GlycolHCID 14798Sodium HydroxideHCID 69568L-Lysine monohydrochloride

Product 1

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

Conditions

Temperature
187 °C

Procedure

300 mmols of L-lysine hydrochloride 1 is neutralized with 300 mmols of NaOH and then 1.2 L of 1,2-propanediol is added. This mixture is heated to 187° C. and is refluxed for 2 hours after removing about the 10% of the solvent when the reaction is first brought to reflux. The yield of α-amino-ε-caprolactam 2 produced by this reaction is about 96%.

Workup

  1. temperatureis refluxed for 2 hours
  2. customafter removing about the 10% of the solvent when the reaction
  3. temperatureto reflux

Sources & evidence

ORD record
ord-57824a47e3ef42aeb3c3e82117fa383d
Source dataset
uspto-grants-2013_02
Patent number
US08367819B2

Reaction notes

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