Acetic Acid → 7-methoxy-3-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 1713088Notes

Reaction equation

HRID 1713088 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]2[C:7](=O)[CH2:8][N:9]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH2:10][CH2:11][C:5]=2[CH:4]=1.C(O)(=O)C.Cl.CCO>[C].[Pd].O1CCOCC1>[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]2[CH2:7][CH2:8][N:9]([S:12]([C:15]3[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=3)(=[O:13])=[O:14])[CH2:10][CH2:11][C:5]=2[CH:4]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 702EthanolHCID 578537987-Methoxy-3-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-benzo[d]azepin-1-one

Product 1

HCID 222509407-methoxy-3-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

7-Methoxy-3-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-benzo[d]azepin-1-one (6.91 g, 20 mmol) (prepared essentially as described by Kanao et al. (1982) Chem. Pharm. Bull. 30:180-88) is added to a mixture of acetic acid (20 ml), 37% hydrochloric acid (8 ml), EtOH (8 ml) and dioxane (80 ml). 1.0 g of 10% palladium-carbon is added to the mixture, and the resulting mixture is hydrogenated under 30-55 psi at rt overnight. The palladium-carbon is removed by filtration, and the filtering cake is washed with MeOH (30 ml×3). The combined organic phase is evaporated to dryness under reduced pressure to give the title compound as a white solid. MS (+VE) m/z 332.1 (M+).

Workup

  1. customThe palladium-carbon is removed by filtration
  2. washthe filtering cake is washed with MeOH (30 ml×3)
  3. customThe combined organic phase is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-32e05a5aa00d4225b56490aafca0a681
Source dataset
uspto-grants-2010_09
Patent number
US07795262B2

Reaction notes

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