Isoamyl Alcohol → 2-(4-Benzylpiperidin-1-yl)-4-amino-7,8-dimethoxyquinazoline hydrochloride

HRID 1577322Notes

Reaction equation

HRID 1577322 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([O:14][CH3:15])[C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[C:4]([Cl:16])[N:3]=1.[CH2:17]([CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O)CC(C)C>C(OCC)C>[ClH:16].[CH2:17]([CH:24]1[CH2:29][CH2:28][N:27]([C:4]2[N:3]=[C:2]([NH2:1])[C:11]3[C:6](=[C:7]([O:14][CH3:15])[C:8]([O:12][CH3:13])=[CH:9][CH:10]=3)[N:5]=2)[CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 31260Isoamyl AlcoholHCID 317384-BenzylpiperidineHCID 129200082-Chloro-4-amino-7,8-dimethoxyquinazoline

Product 1

HCID 205064012-(4-Benzylpiperidin-1-yl)-4-amino-7,8-dimethoxyquinazoline hydrochlorideYield 60%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

4-Amino-2-chloro-7,8-dimethoxyquinazoline (2.40 g., 10 mmole), 4-benzylpiperidine (1.93 g., 11 mmole) and 50 ml. of isoamyl alcohol were heated at reflux under a nitrogen atmosphere for two hours and cooled to room temperature. Diethyl ether (50 ml.) was added and the mixture allowed to stand in the refrigerator for two days. The precipitated solid was collected by filtration and recrystallized from ethanol/diethyl ether to afford 2.50 g. (60%) of the title compound, M.P. 216°-217° C.

Workup

  1. temperatureat reflux under a nitrogen atmosphere for two hours
  2. filtrationThe precipitated solid was collected by filtration
  3. customrecrystallized from ethanol/diethyl ether
  4. customto afford 2.50 g

Sources & evidence

ORD record
ord-b9df01931ff640748e40147d4a8585be
Source dataset
uspto-grants-1981_09
Patent number
US04287341

Reaction notes

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