4-Toluenesulfonyl chloride → N-2-chlorobenzyl-1-methyl-2-(2-thienyl)ethylamine

HRID 1638153Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH:7](O)[CH3:8].C(N(CC)CC)C.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[Cl:28][C:29]1[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:31][NH2:32]>C1(C)C=CC=CC=1.O>[Cl:28][C:29]1[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=1[CH2:31][NH:32][CH:7]([CH3:8])[CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-(2-thienyl)-2-propanol (14.4 g) and triethylamine (10.5 g) in 60 ml of toluene, a solution of p-toluensulfonylchloride (19.0 g) into 40 ml of toluene is added dropwise. The mixture is stirred for 24 hours. The precipitate of triethylamine HCl is removed by filtration and the filtrate is added dropwise to a solution of 2-chlorobenzylamine (28.3 g, 0.2 moles) into 100 ml of toluene at the reflux temperature over the course of 12-14 hours. The heating is continued for an additional 6 hours. Thereafter the mixture is cooled to 80° C., 200 ml of water is added, and the mixture is further cooled to room temperature. The organic phase is separated and acidified with 3 M hydrochloric acid. The resulting hydrochloride is collected by filtration and washed with acetone to yield, after drying, 16.4 g (61.7%) of N-2-chlorobenzyl-1-methyl-2-(2-thienyl)ethylamine HCl having a m.p. 164-165° C.

Workup

customThe precipitate of triethylamine HCl is removed by filtration
waitThe heating is continued for an additional 6 hours
temperaturethe mixture is further cooled to room temperature
customThe organic phase is separated
filtrationThe resulting hydrochloride is collected by filtration
washwashed with acetone
customto yield
customafter drying

Sources & evidence

ORD record: ord-5573e7d7386c454f99d521d57a36301a
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06043368

Reaction notes

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