N-Methylhomoveratrylamine → HCID 21279707, compound

HRID 2291261Notes

Reaction equation

HRID 2291261 reaction equation
[Cl:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.[CH3:17][NH:18][CH2:19][CH2:20][C:21]1[CH:30]=[CH:29][C:26]([O:27][CH3:28])=[C:23]([O:24][CH3:25])[CH:22]=1>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[ClH:1].[CH3:17][N:18]([CH2:19][CH2:20][C:21]1[CH:30]=[CH:29][C:26]([O:27][CH3:28])=[C:23]([O:24][CH3:25])[CH:22]=1)[C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 77039N-MethylhomoveratrylamineHCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamine

Product 1

HCID 21279707HCID 21279707, compound

Reagents, catalysts & solvents 1

HCID 66133Benzyl triethylammonium chlorideCatalyst

Conditions

Temperature
110 °C

Procedure

A mixture of 5 g of 2-chloro-4-amino-6,7-dimethoxy quinazoline, 30 g of N-methyl-homoveratryl amine (Lloydia 33, 15-18) and 1 g of triethylbenzyl ammonium chloride was heated with stirring to 110° C. over a 3 hour period. Then the excess of N-methyl-homoveratryl amine was distilled off in vacuo. On standing in the cold, a precipitate was formed from the solution of the evaporation residue in acetone. After filtration with activated charcoal, the precipitate was recrystallized from methanol. The N-methyl-N-(4-amino-6,7-dimethoxy-quinazolin-2-yl)-homoveratryl amine hydrochloride obtained melted at 265°-270° C. with decomposition.

Workup

  1. temperaturewas heated
  2. distillationThen the excess of N-methyl-homoveratryl amine was distilled off in vacuo
  3. customa precipitate was formed from the solution of the evaporation residue in acetone
  4. filtrationAfter filtration with activated charcoal
  5. customthe precipitate was recrystallized from methanol

Sources & evidence

ORD record
ord-2d31fe75442d45cf8affd6b7693aabe7
Source dataset
uspto-grants-1989_01
Patent number
US04795750

Reaction notes

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