Methylamine → HCID 15132275, compound

HRID 982409Notes

Reaction equation

[CH3:1][NH2:2].COS([CH2:8][CH2:9][CH:10]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1)(=O)=O>O1CCCC1.C(OCC)(=O)C>[CH3:1][NH:2][CH2:8][CH2:9][CH:10]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 22 °C

Procedure

Methylamine (37.2 ml of a 40% by weight aqueous solution, 481 mmole) was added to a 250 ml flask containing 4.47 g (12.0 mmole) of 3-phenyl-4-(4-trifluoromethylphenyl)butane sulfonic acid methyl ester dissolved in 50 ml of tetrahydrofuran. The resulting solution was stirred overnight at room temperature (22° C.) and concentrated under reduced pressure to provide a residue. The residue was dissolved in ethyl acetate and the resulting solution was washed with water and a saturated brine solution. The organic solution was dried over anhydrous sodium sulfate and the volatiles were removed under reduced pressure to provide 3.5 g of N-methyl-3-phenyl-4-(4-trifluoromethylphenyl)butanamine as an oil. A sample of the oil was crystallized from an acetone/diethyl ether solution containing 1.5 equivalents of concentrated hydrochloric acid to yield N-methyl-3-phenyl-4-(4-trifluoromethylphenyl)butanamine hydrochloride as white crystals. mp=156°-157.5° C.

Workup

concentrationconcentrated under reduced pressure
customto provide a residue
washthe resulting solution was washed with water
dry with materialThe organic solution was dried over anhydrous sodium sulfate
customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record: ord-15aa05f6a57f40ca8bcfca672d673dbd
Source dataset: uspto-grants-1991_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04996235

Reaction notes

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