Tripropylamine → HCID 20146416, compound

HRID 570018Notes

Reaction equation

HRID 570018 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[N:3]=1.[Cl:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:24]=1.C(N(CCC)CCC)CC>C(O)CC(C)C>[ClH:22].[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[C:4]([N:16]2[CH2:21][CH2:20][N:19]([C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)[CH2:18][CH2:17]2)[N:3]=1

Participants

5

Reactant 3

HCID 7616TripropylamineHCID 119282-ChloroquinolineHCID 6162672-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazoline

Product 1

HCID 20146416HCID 20146416, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

Mixed were 0.72 g (2.5 mmol) of 4-amino-6,7-dimethoxy-2-piperazinoquinazoline, 0.63 g (3.9 mmol) of 2-chloroquinoline, 0.43 g (3 mmol) of tri-n-propylamine and 15 ml of isoamyl alcohol. The mixture was refluxed for 16 hours. After cooling the reaction mixture, the resultant crystals were collected by filtration, followed by their dissolution in a mixed solvent of 10 ml of dichloromethane and 10 ml of methanol. To the solution, 2 ml of a 20% ethanol solution of hydrochloric acid was added. The solvents were distilled off to obtain 0.90 g of the above-identified compound (yield: 80%).

Workup

  1. additionMixed
  2. temperatureThe mixture was refluxed for 16 hours
  3. temperatureAfter cooling the reaction mixture
  4. filtrationthe resultant crystals were collected by filtration
  5. dissolutionfollowed by their dissolution in a mixed solvent of 10 ml of dichloromethane and 10 ml of methanol
  6. additionTo the solution, 2 ml of a 20% ethanol solution of hydrochloric acid was added
  7. distillationThe solvents were distilled off

Sources & evidence

ORD record
ord-39008dc58ba04929a782102bfe57cdbc
Source dataset
uspto-grants-1988_03
Patent number
US04734418

Reaction notes

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