Potassium Carbonate → 7-Methanesulfonyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 395271Notes

Reaction equation

HRID 395271 reaction equation
C([N:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][C:13]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:14][C:7]=2[CH2:6][CH2:5]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>Cl>[CH3:18][S:15]([C:13]1[CH:12]=[CH:11][C:8]2[CH2:9][CH2:10][NH:4][CH2:5][CH2:6][C:7]=2[CH:14]=1)(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 112656343-Acetyl-7-methylsulfonyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 117362667-Methanesulfonyl-2,3,4,5-tetrahydro-1H-benzo[d]azepineYield 32%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3-acetyl-7-methylsulphonyl-2,3,4,5-tetrahydro-1H-3-benzazepine (1.75 g, 6.55 mmol) in 5 M hydrochloric acid was heated at reflux for 18 h. The reaction mixture was then cooled to room temperature, basified to pH 12 with potassium carbonate and the solvent evaporated in vacuo. The solid residue was then extracted with ethyl acetate (5×60 ml) and the combined organics dried (Na2SO4). The solvent was then evaporated in vacuo to give the title compound (450 mg, 32%) as a pale yellow oil.

Workup

  1. temperatureat reflux for 18 h
  2. customthe solvent evaporated in vacuo
  3. extractionThe solid residue was then extracted with ethyl acetate (5×60 ml)
  4. dry with materialthe combined organics dried (Na2SO4)
  5. customThe solvent was then evaporated in vacuo

Sources & evidence

ORD record
ord-10f622db23034da5ad3582e8651b7200
Source dataset
uspto-grants-2003_08
Patent number
US06605607B1

Reaction notes

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