Triethylamine → 4-amino-6,7-dimethoxy-2-[4-(N-n-butylcarbamoyl)piperidino]quinazoline hydrochloride

HRID 1389150Notes

Reaction equation

HRID 1389150 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]([Cl:16])[N:3]=1.[CH2:17]([NH:21][C:22]([CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)=[O:23])[CH2:18][CH2:19][CH3:20].C(N(CC)CC)C>C(O)CCC>[ClH:16].[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:27]2[CH2:28][CH2:29][CH:24]([C:22](=[O:23])[NH:21][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:25][CH2:26]2)[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 16228130N-butylpiperidine-4-carboxamide

Product 1

HCID 202981034-amino-6,7-dimethoxy-2-[4-(N-n-butylcarbamoyl)piperidino]quinazoline hydrochlorideYield 26.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

4-Amino-2-chloro-6,7-dimethoxyquinazoline (1.2 g), 4-(N-n-butylcarbamoyl)piperidine (1.01 g) and triethylamine (2.52 g) in n-butanol (105 ml) were heated under reflux for 24 hours. The mixture was then cooled, the solvent evaporated in vacuo, and the resultant solid shaken with chloroform and water. The solid product was collected by filtration, and recrystallised twice from ethanol to give 4-amino-6,7-dimethoxy-2-[4-(N-n-butylcarbamoyl)piperidino]quinazoline hydrochloride (0.57 g), m.p. 263°-264°.

Workup

  1. temperatureunder reflux for 24 hours
  2. temperatureThe mixture was then cooled
  3. customthe solvent evaporated in vacuo
  4. filtrationThe solid product was collected by filtration
  5. customrecrystallised twice from ethanol

Sources & evidence

ORD record
ord-0072ec72283d44459a5f3c7d2791352c
Source dataset
uspto-grants-1981_01
Patent number
US04243666

Reaction notes

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