Triethylamine → N-(4-acetoxyphenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline

HRID 35240Notes

Reaction equation

HRID 35240 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH:9]([CH3:15])[NH:8][CH2:7][CH2:6]2.C(N(CC)CC)C.[C:23]([O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34](Cl)=[O:35])=[CH:29][CH:28]=1)(=[O:25])[CH3:24]>C(Cl)(Cl)Cl>[C:23]([O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][C:34]([N:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH:9]2[CH3:15])=[O:35])=[CH:29][CH:28]=1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 103026,7-Dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinolineHCID 182488Benzeneacetyl chloride, 4-(acetyloxy)-

Product 1

HCID 21295810N-(4-acetoxyphenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinolineYield 90.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline (20.0 g, 0.097 m) and triethylamine (9.8 ml, 0.097 m) in chloroform (200 ml) under nitrogen was added dropwise a solution of 4-acetoxyphenylacetyl chloride (20.3 g, 0.097 m) in 50 ml chloroform and the mixture stirred at ambient temperature for 16 hours. The mixture was washed with 10% HCl (3×200 ml), water (200 ml), saturated sodium carbonate (3×150 ml) and water (200 ml) and the chloroform layer dried over MgSO4. Evaporation of the solvent afforded 33.0 g of N-(4-acetoxyphenylacetyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylisoquinoline as a pale yellow oil (89% yield).

Workup

  1. washThe mixture was washed with 10% HCl (3×200 ml), water (200 ml), saturated sodium carbonate (3×150 ml) and water (200 ml)
  2. dry with materialthe chloroform layer dried over MgSO4
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-03615a9232a543cdbced5ab10d137e44
Source dataset
uspto-grants-1988_08
Patent number
US04766131

Reaction notes

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