Hydrochloric Acid → 1-(p-Toluidinomethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride

HRID 27167Notes

Reaction equation

[ClH:1].C(OC([N:12]([CH2:20][CH:21]1[C:30]2[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=2)[CH2:24][CH2:23][NH:22]1)[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)=O)C1C=CC=CC=1.Cl>C(O)(=O)C>[ClH:1].[ClH:1].[C:16]1([CH3:19])[CH:15]=[CH:14][C:13]([NH:12][CH2:20][CH:21]2[C:30]3[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=3)[CH2:24][CH2:23][NH:22]2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-(N-benzyloxycarbonyl-p-toluidinomethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (470 mg), acetic acid (4.7 ml) and conc. hydrochloric acid (4.7 ml) was heated for 1 hour at 100° C. The reaction mixture was concentrated to dryness under reduced pressure and the residue was dissolved in methanol. To the solution was added ethyl acetate and the precipitating crystals were collected by filtration to give 1-(p-toluidinomethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride (270 mg), mp 180° to 184° C.

Workup

concentrationThe reaction mixture was concentrated to dryness under reduced pressure
dissolutionthe residue was dissolved in methanol
additionTo the solution was added ethyl acetate
filtrationthe precipitating crystals were collected by filtration

Sources & evidence

ORD record: ord-a7e126d383c242528948ea4143ce1498
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04220647

Reaction notes

Loading…