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

HRID 33204Notes

Reaction equation

HRID 33204 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-methylsulfonyl-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-baa428799dcc4f4d9fcc551287b20dc2
Source dataset
uspto-grants-2008_09
Patent number
US07429579B2

Reaction notes

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