3-Fluorobenzyl chloride → {[2-(3-Fluorobenzyloxy)cyclohexyl]phenylmethyl}-dimethylamine hydrochloride

HRID 459667Notes

Reaction equation

[CH3:1][N:2]([CH:4]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[OH:11])[CH3:3].CC([O-])(C)C.[K+].[F:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28][Cl:29]>CS(C)=O>[ClH:29].[F:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28][O:11][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH:5]1[CH:4]([N:2]([CH3:1])[CH3:3])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

1.00 g (4.29 mmole) of the 2-(dimethylaminophenylmethyl)cyclohexanol prepared according to Example 1 (3rd stage) were dissolved in 5 ml dimethylsulfoxide, analytical grade, and 503 mg (4.48 mmole) potassium tert-butylate were added at 50° C. The mixture was then heated to 100° C. and 323 μl (2.61 mmole) 3-fluorobenzyl chloride were added. This addition was repeated twice more after in each case two hours, and the reaction mixture was then heated at 100° C. for a further 15 hours. Working up was carried out according to Example 1 (4th stage), as a result of which 166 mg {[2-(3-fluorobenzyloxy)cyclohexyl]phenylmethyl}-dimethylamine hydrochloride (11% of theoretical), which decomposes from 203° C. on heating, were obtained.

Workup

additionThis addition
customin each case two hours
temperaturethe reaction mixture was then heated at 100° C. for a further 15 hours

Sources & evidence

ORD record: ord-9064e9ed3e0640a4a47555c114029fb7
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: USRE039530E1

Reaction notes

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