Hydrochloric Acid → N-(4-aminophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline dihydrochloride

HRID 35234Notes

Reaction equation

HRID 35234 reaction equation
[ClH:1].[N+:2]([C:5]1[CH:26]=[CH:25][C:8]([CH2:9][CH2:10][N:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][C:15]([O:23][CH3:24])=[C:16]([O:21][CH3:22])[CH:17]=3)[CH2:12]2)=[CH:7][CH:6]=1)([O-])=O.Cl>CO.[Pd]>[ClH:1].[ClH:1].[NH2:2][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][CH2:10][N:11]2[CH2:20][CH2:19][C:18]3[C:13](=[CH:14][C:15]([O:23][CH3:24])=[C:16]([O:21][CH3:22])[CH:17]=3)[CH2:12]2)=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 14230287N-(4-nitrophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline hydrochloride

Product 1

HCID 14230289N-(4-aminophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline dihydrochlorideYield 178.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-(4-Nitrophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline hydrochloride (14.1 g, 0.037 m) was dissolved in methanol (500 ml) containing 10 ml of conc HCl and hydrogenated in a Parr apparatus over 5% Pd/C catalyst (1.5 g) at 40 psi for 1 hour. The catalyst was removed by filtration and the solvent volume reduced to ca 150 ml at an aspirator. Ethanol (100 ml) and ether (50 ml) were added and the mixture was hot filtered and allowed to stand overnight. The crystallized solid was collected by filtration and vacuum dried to give 12.8 g of N-(4-aminophenethyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline dihydrochloride, m.p. 259°-261°.

Workup

  1. customThe catalyst was removed by filtration
  2. additionEthanol (100 ml) and ether (50 ml) were added
  3. filtrationthe mixture was hot filtered
  4. filtrationThe crystallized solid was collected by filtration and vacuum
  5. customdried

Sources & evidence

ORD record
ord-9700d17c31a3457abafd090628ddb158
Source dataset
uspto-grants-1988_08
Patent number
US04766131

Reaction notes

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