Methanol → 6-Methyl-1,4-oxazepane hydrochloride

HRID 515454Notes

Reaction equation

HRID 515454 reaction equation
COC1C=CC(C[N:8]2[CH2:14][CH:13]([CH3:15])[CH2:12][O:11][CH2:10][CH2:9]2)=CC=1.[Cl:18]C(OC(Cl)C)=O.CO>ClCCCl>[ClH:18].[CH3:15][CH:13]1[CH2:12][O:11][CH2:10][CH2:9][NH:8][CH2:14]1

Participants

5

Reactant 3

HCID 887MethanolHCID 5213051-Chloroethyl chloroformateHCID 667188184-(4-Methoxy-benzyl)-6-methyl-[1,4]oxazepane

Product 1

HCID 667185826-Methyl-1,4-oxazepane hydrochlorideYield 83%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-(4-methoxy-benzyl)-6-methyl-[1,4]oxazepane (3.24 g, 13.8 mmol) in 1,2-dichloroethane (23 ml) was added 1-chloroethyl chloroformate (4.93 g, 34.5 mmol) at room temperature. The mixture was refluxed for 7 hours. The reaction mixture was cooled to room temperature and then methanol (30 ml) was added. The mixture was refluxed for 5 hours and concentrated in vacuo. This crude product was washed with hexane, dried under reduced pressure to afford 6-methyl-[1,4]oxazepane hydrochloride as white solid (1.73 g, 83%).

Workup

  1. temperatureThe mixture was refluxed for 7 hours
  2. temperatureThe mixture was refluxed for 5 hours
  3. concentrationconcentrated in vacuo
  4. washThis crude product was washed with hexane
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-752d6f53e5654681bf9e799f865ae4ba
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Reaction notes

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