Dimethylamine → HCID 66773007, compound

HRID 1644559Notes

Reaction equation

HRID 1644559 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](SC)=[N:7][CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1.[CH3:23][NH:24][CH3:25]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:24]([CH3:25])[CH3:23])=[N:7][CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 667722916-Chloro-1-methylthio-4-(4-nitrophenyl)-3,4-dihydroisoquinoline2×

Product 1

HCID 66773007HCID 66773007, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

400 mg of 6-chloro-1-methylthio-4-(4-nitrophenyl)-3,4-dihydroisoquinoline (compound 1) were heated with 20 ml of dimethylamine in THF at 120° C. in a shaking autoclave under inert gas for 20 hours. Removal of the solvent by distillation was followed by MPLC chromatography on an MPRC cartridge with a mixture of 10 parts by volume of ethyl acetate, 5 parts by volume of n-heptane, 5 parts by volume of dichloromethane, 5 parts by volume of methanol and 1 part by volume of concentrated aqueous ammonia solution. Semisolid, partly amorphous product.

Workup

  1. customRemoval of the solvent
  2. distillationby distillation
  3. additionwas followed by MPLC chromatography on an MPRC cartridge with a mixture of 10 parts by volume of ethyl acetate, 5 parts by volume of n-heptane, 5 parts by volume of dichloromethane, 5 parts by volume of methanol and 1 part by volume of concentrated aqueous ammonia solution

Sources & evidence

ORD record
ord-e215130240ee4f159a8a831eabcf6e91
Source dataset
uspto-grants-2012_02
Patent number
US08124621B2

Reaction notes

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