Dimethylformamide → HCID 21330001, compound

HRID 614064Notes

Reaction equation

HRID 614064 reaction equation
Br.Br.[NH2:3][CH:4]([C:6]1[C:15]2[C:10](=[CH:11][C:12]([O:18][CH3:19])=[C:13]([O:16][CH3:17])[CH:14]=2)[CH2:9][CH2:8][N:7]=1)[CH3:5].C(=O)([O-])[O-].[K+].[K+].[CH3:26][N:27]([CH3:30])C=O>>[CH3:19][O:18][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][C:13]=1[O:16][CH3:17])[C:6]1=[C:4]([CH3:5])[N:3]=[C:26]([NH:27][C:30]3[C:6]([CH3:4])=[CH:15][CH:10]=[CH:11][C:12]=3[CH3:13])[N:7]1[CH2:8][CH2:9]2

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 21330002HCID 21330002, compound

Product 1

HCID 21330001HCID 21330001, compound

Procedure

2.9 g 2,6-dimethylphenylisocyanide dichloride is added to a suspension of 5 g of 1-(1-aminoethyl)-3,4-dihydro-6,7-dimethoxyisoquinoline dihydrobromide in 100 ml dimethylformamide. 3.6 g of anhydrous potassium carbonate are then added. The suspension is stirred and warmed at 60° for 6 hours. The potassium carbonate is filtered off and washed with dimethylformamide. The washings and filtrate are concentrated in a vacuum, and the residue is chromatographed on silicagel using CHCl3 /CH3OH (95:5) as eluant to give the title compound as the free base; M.Pt. 234°-236°.

Workup

  1. temperaturewarmed at 60° for 6 hours
  2. filtrationThe potassium carbonate is filtered off
  3. washwashed with dimethylformamide
  4. concentrationThe washings and filtrate are concentrated in a vacuum
  5. customthe residue is chromatographed on silicagel

Sources & evidence

ORD record
ord-0b697fa016714c06b5fd86fe8d485770
Source dataset
uspto-grants-1979_03
Patent number
US04143143

Reaction notes

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