Water → (+/-) 7-Amino-1,2-dimethyl-tetrahydroisoquinoline

HRID 2297612Notes

Reaction equation

[I-].[NH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N+:9]([CH3:13])=[CH:10]2)=[CH:5][CH:4]=1.[CH3:14][Mg]Cl.O>O1CCCC1>[NH2:2][C:3]1[CH:12]=[C:11]2[CH:6]([CH2:7][CH2:8][N:9]([CH3:13])[CH:10]2[CH3:14])[CH2:5][CH:4]=1

Participants

Conditions

Temperature: -78 °C

Procedure

(±) 7-Amino-2-methyl-3,4-dihydroisoquinolinium iodide (0.50 g, 1.7 mmol) was suspended in anhydrous tetrahydrofuran (50 ml) and cooled to −78° C. The cooled solution was treated with methyl magnesium chloride (2.14 ml of a 3M solution in THF, 6.96 mmol), added as a single portion. The reaction was allowed to reach 25° C. over 18 h before being poured into water (50 ml). The organic solvent was removed in vacuo and the organic product extracted into dichloromethane. Drying over magnesium sulfate and evaporation in vacuo furnished the title compound as a pale yellow oil (0.3 g, 98%). For ease of handling the product was converted into a monohydrochloride.

Workup

additionadded as a single portion
customThe organic solvent was removed in vacuo
extractionthe organic product extracted into dichloromethane
dry with materialDrying over magnesium sulfate and evaporation in vacuo

Sources & evidence

ORD record: ord-2e8d98661ca5413794e11261181fad77
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492378B1

Reaction notes

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