Toluene → 1-[1-(4-Chlorophenyl)cyclobutyl]-N,N,3-trimethylbutan-1-amine--hydrogen chloride--water (1/1/1)

HRID 1651545Notes

Reaction equation

Cl.[CH3:2][N:3]([CH:5]([C:10]1([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:13][CH2:12][CH2:11]1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:4].C1(C)C=CC=CC=1.CC([OH:31])C>O>[OH2:31].[ClH:20].[CH3:2][N:3]([CH:5]([C:10]1([C:14]2[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[CH2:13][CH2:12][CH2:11]1)[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:4]

Participants

Conditions

Temperature: 72 °C

Procedure

A sample (5 g) of N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine hydrochloride was heated with a mixture of toluene (30 ml) and propan-2-ol (3 ml) to 90° C. and allowed to cool to 72° C. Water (0.9 ml) was added and the mixture cooled to 25° C. and then placed in an ice-water bath for 30 minutes. A solid was collected by filtration, washed with cold toluene and dried by suction at ambient temperature to give N,N-dimethyl-1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutylamine hydrochloride monohydrate [m.p. 193°-195° C. (shrinks 150°-155° C.)].

Workup

temperaturethe mixture cooled to 25° C.
filtrationA solid was collected by filtration
washwashed with cold toluene
customdried by suction at ambient temperature

Sources & evidence

ORD record: ord-8b2b771d0b3d40b391b3cb68acbaa4c9
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04929629

Reaction notes

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