Water → 1,2,3,4-Tetrahydro-1,1,2-trimethyl-7-isoquinolinamine

HRID 650953Notes

Reaction equation

[I-].[NH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N+:9]([CH3:14])=[C:10]2[CH3:13])=[CH:5][CH:4]=1.[CH3:15][Mg]Cl.O>C1COCC1>[NH2:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([CH3:14])[C:10]2([CH3:15])[CH3:13])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: -78 °C

Procedure

7-Amino-1,2-dimethyl-3,4-dihydroisoquinolinium iodide (1.44 g, 4.8 mmol) was suspended in THF (200 ml), cooled to −78° C. and treated with methyl magnesium chloride (10 ml of a 3M solution in THF) added as a single portion. The reaction was allowed to reach room temperature over 18 h and poured into water (200 ml). The organic solvent was removed in vacuo and the resultant oily residue extracted into dichloromethane (3×50 ml). Evaporation in vacuo and chromatography through silica gel eluting with (0.5% 0.88 NH3: 4.5% CH3OH: 95% CH2Cl2) yielded the title compound as a yellow oil (0.07 g, 8%). 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 resultant oily residue extracted into dichloromethane (3×50 ml)
customEvaporation in vacuo and chromatography through silica gel eluting with (0.5% 0.88 NH3: 4.5% CH3OH: 95% CH2Cl2)

Sources & evidence

ORD record: ord-f53df890d267462b9a67445e90af45f4
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06277861B1

Reaction notes

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