Methyl iodide → HCID 22406873, compound

HRID 440475Notes

Reaction equation

HRID 440475 reaction equation
CI.[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[C:11]1([CH:15]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=3)[CH2:18][CH2:17][NH:16]2)[CH2:14][CH2:13][CH2:12]1.[C:29](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[C:11]1([CH:15]2[C:24]3[C:19](=[CH:20][C:21]([O:27][CH3:28])=[C:22]([O:25][CH3:26])[CH:23]=3)[CH2:18][CH2:17][N:16]2[CH3:29])[CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22406894HCID 22406894, compound

Product 1

HCID 22406873HCID 22406873, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of methyl iodide (1.9 g) in acetone (20 ml) was added dropwise to a stirred suspension of 1-[1-(2,4-dichlorophenyl)cyclobutyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (4 g prepared as described in Example RC9) and anhydrous potassium carbonate (3.1 g) in acetone (70 ml). The mixture was stirred at ambient temperature for 90 minutes and the solvent removed by evaporation. Water was added and the mixture extracted with ether. The ether layer yielded 1-[1-(2,4-dichlorophenyl)cyclobutyl]-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline as an oil. A portion of this oil was characterised by conversion into its 1.5 oxalate salt, m.p. 125°-132° C.

Workup

  1. customthe solvent removed by evaporation
  2. additionWater was added
  3. extractionthe mixture extracted with ether

Sources & evidence

ORD record
ord-bd1943f6d7964225824729a2f255c1f1
Source dataset
uspto-grants-1996_05
Patent number
US05519034

Reaction notes

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