Sodium Hydroxide → 3-Aminoazepan-2-one hydrochloride

A stirred mixture of L-lysine hydrochloride 1 (55 g, 300 mmol) and NaOH (12 g, 300 mmol) in 1,2-propanediol (1.2 L) is heated to reflux. A Dean-Stark trap is used to withdraw the first 120 mL of condensed solvent. The reaction solution is refluxed for an additional 2 hours until all starting material is consumed (which maybe determined by 1H NMR). The solution is cooled and is concentrated under vacuum. Ethanol is used to completely dissolve the α-amino-ε-caprolactam 2. Byproduct NaCl is removed by filtration. The filtrate is concentrated and the resulting crude α-amino-ε-caprolactam 2 is dissolved in water. After acidification to pH 6 with addition of concentrated HCl and subsequent partial concentration, crystals maybe formed at room temperature to afford α-amino-ε-caprolactam hydrochloride (36.5 g) in 74% yield.

1. temperatureis heated to reflux
2. customto withdraw
3. customthe first 120 mL of condensed solvent
4. temperatureThe reaction solution is refluxed for an additional 2 hours until all starting material
5. customis consumed (which
6. temperatureThe solution is cooled
7. concentrationis concentrated under vacuum
8. dissolutionto completely dissolve the α-amino-ε-caprolactam 2
9. customByproduct NaCl is removed by filtration
10. concentrationThe filtrate is concentrated
11. dissolutionthe resulting crude α-amino-ε-caprolactam 2 is dissolved in water
12. additionAfter acidification to pH 6 with addition of concentrated HCl and subsequent partial concentration, crystals
13. custommaybe formed at room temperature

ORD-Eintrag

ord-6cddf3beac3b4a03a18aa4d270c3ea1a

Quelldatensatz

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07977450B2