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

HRID 543743Notes

Reaction equation

HRID 543743 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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 204605451-(N-benzyloxycarbonyl-p-toluidinomethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 204605361-(p-Toluidinomethyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline dihydrochlorideYield 144%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

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

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

Sources & evidence

ORD record
ord-3c5a907aacf34aab964df729c81ecace
Source dataset
uspto-grants-1984_05
Patent number
US04447436

Reaction notes

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