2-Chloroethyl chloroformate → 5-Methyl-1,4-oxazepane hydrochloride

HRID 515445Notes

Reaction equation

HRID 515445 reaction equation
C([N:8]1[CH:14]([CH3:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:16]C(OCCCl)=O>ClCCCl>[ClH:16].[CH3:15][CH:14]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9][NH:8]1

Participants

4

Reactant 2

HCID 123052-Chloroethyl chloroformateHCID 667187904-Benzyl-5-methyl-[1,4]oxazepane

Product 1

HCID 667186395-Methyl-1,4-oxazepane hydrochlorideYield 78.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-benzyl-5-methyl-[1,4]oxazepane (0.30 g, 1.4 mmol) in 1,2-dichloroethane (3 mL) was added chloroethyl chloroformate (0.56 mL, 7 mmol) at room temperature. The mixture was refluxed for 10 hours and concentrated. The resulting residue was dissolved in methanol (5 mL) and the solution was refluxed for one hour. After concentration, the residual material was triturated, washed with ethyl acetate and collected by filtration to afford 5-methyl-[1,4]oxazepane hydrochloride (0.16 g, 1.1 mmol, 76%) as a white solid.

Workup

  1. temperatureThe mixture was refluxed for 10 hours
  2. concentrationconcentrated
  3. dissolutionThe resulting residue was dissolved in methanol (5 mL)
  4. temperaturethe solution was refluxed for one hour
  5. concentrationAfter concentration
  6. customthe residual material was triturated
  7. washwashed with ethyl acetate
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-337a7b879283470cba51f99f8306b20f
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Reaction notes

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