Ethanol → 2H-Azepin-2-one, 3-aminohexahydro-

HRID 1269747Notes

Reaction equation

HRID 1269747 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[NH2:10][CH:11]([C:17]([OH:19])=O)[CH2:12][CH2:13][CH2:14][CH2:15][NH2:16].C(O)C>Cl[Si](C)(C)C.C1(C)C(C)=CC=CC=1>[NH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]1=[O:19]

Participants

6

Reactant 3

HCID 702EthanolHCID 866Lysine, DL-HCID 13838Hexamethyldisilazane

Product 1

HCID 1024632H-Azepin-2-one, 3-aminohexahydro-Yield 60.5%

Reagents, catalysts & solvents 2

HCID 6397ChlorotrimethylsilaneCatalystHCID 7237O-XyleneSolvent

Procedure

Hexamethyldisilazane (30 ml) and chloro-trimethylsilane (several drops) were added to a suspension of DL-lysine (3.0 g, 20.5 mmol) in xylene (270 ml) at room temperature, and the reaction was carried out at 140° C. for 48 hours. The reaction mixture was cooled and then poured into ethanol (600 ml), and the resulting mixture was concentrated. The resulting residue was suspended in chloroform, followed by filtration and concentration, whereby 3-amino-2-azepanone (1.59 g, 60%) was obtained.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationthe resulting mixture was concentrated
  3. filtrationfollowed by filtration and concentration

Sources & evidence

ORD record
ord-1cfd9bce24cd424a9998a1c91503d6e0
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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