Hydrochloric Acid → 3-Fluoro-N-(5-methylaminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide

HRID 492087Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:21]=[CH:20][C:19]3[CH:18]([CH2:22][NH:23][CH:24]=O)[CH2:17][CH2:16][CH2:15][C:14]=3[CH:13]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.B.C1COCC1.Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][C:12]2[CH:21]=[CH:20][C:19]3[CH:18]([CH2:22][NH:23][CH3:24])[CH2:17][CH2:16][CH2:15][C:14]=3[CH:13]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of 0.17 grams (0.469 mmoles) 3-fluoro-N-(5-formylaminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide in 5 mL THF was added 2 mL 1.0M borane-THF. The reaction mixture was stirred at 23° C. for 18 hours. 1.0 mL 6N hydrochloric acid was added and the mixture was heated under reflux for 15 minutes. The solution was concentrated under reduced pressure and the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. 3-Fluoro-N-(5-methylaminomethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzenesulfonamide was isolated as the crystalline oxalate salt, 0.05 grams (24%), m.p. 135-136° C., M+H=349.

Workup

temperaturethe mixture was heated
temperatureunder reflux for 15 minutes
concentrationThe solution was concentrated under reduced pressure
customthe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
dry with materialThe organic phase was dried (magnesium sulfate)
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-b7032a57914543d583a85c6c3002fca5
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531577B2

Reaction notes

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