Methyl iodide → 3-Acetyl-7-methylsulfonyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 33203Notes

Reaction equation

S([O-])([O-])=O.[Na+].[Na+].[C:7](=O)([O-])O.[Na+].[C:12]([N:15]1[CH2:21][CH2:20][C:19]2[CH:22]=[CH:23][C:24]([S:26](Cl)(=[O:28])=[O:27])=[CH:25][C:18]=2[CH2:17][CH2:16]1)(=[O:14])[CH3:13].CI>O.O1CCCC1>[C:12]([N:15]1[CH2:21][CH2:20][C:19]2[CH:22]=[CH:23][C:24]([S:26]([CH3:7])(=[O:28])=[O:27])=[CH:25][C:18]=2[CH2:17][CH2:16]1)(=[O:14])[CH3:13]

Participants

Conditions

Temperature: 75 °C

Procedure

To a stirred solution of sodium sulphite (1.60 g, 12.6 mmol) and sodium hydrogen carbonate (1.14 g, 13.56 mmol) in water (25 ml) was added 3-acetyl-7-chlorosulfonyl-2,3,4,5-tetrahydro-1H-3-benzazepine (2.6 g, 9.04 mmol) in tetrahydrofuran (10 ml). The reaction mixture was then heated at 75° C. for 2 h, cooled to 30° C. and methyl iodide (2.8 ml, 45.20 mmol) added. After stirring at 50° C. for 24 h, the reaction mixture was cooled to room temperature and partitioned between water (50 ml) and ethyl acetate (100 ml). The aqueous layer was then separated and further extracted with ethyl acetate (2×80 ml). The combined organics were then dried (Na2SO4) and the solvent removed in vacuo to give the title compound (1.77 g, 73%) as a pale yellow solid.

Workup

temperaturecooled to 30° C.
temperaturethe reaction mixture was cooled to room temperature
custompartitioned between water (50 ml) and ethyl acetate (100 ml)
customThe aqueous layer was then separated
extractionfurther extracted with ethyl acetate (2×80 ml)
dry with materialThe combined organics were then dried (Na2SO4)
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-38a99d1ea04842b5afd660197151a66f
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429579B2

Reaction notes

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