Triethylamine → HCID 20298113, compound

HRID 1389164Notes

Reaction equation

HRID 1389164 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.Cl.[NH:18]1[CH2:23][CH2:22][CH:21]([CH2:24][C:25]([OH:27])=[O:26])[CH2:20][CH2:19]1.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:18]2[CH2:23][CH2:22][CH:21]([CH2:24][C:25]([OH:27])=[O:26])[CH2:20][CH2:19]2)[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 155657754-Piperidineacetic acid hydrochloride

Product 1

HCID 20298113HCID 20298113, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

4-Amino-2-chloro-6,7-dimethoxyquinazoline (17.3 g), piperidine-4-acetic acid hydrochloride (12.0 g) and triethylamine (20 ml) in n-butanol (500 ml) were stirred under reflux for 20 hours. The mixture was then cooled to 0°-4° and the separated product collected. The solid was slurried with acetone (100 ml), filtered, slurried with chloroform (100 ml), filtered and washed with ether to give 4-amino-2-(4-carboxymethylpiperidino)-6,7-dimethoxyquinazoline hydrochloride (19.0 g). A sample was recrystallised from acetic acid and had an m.p. of 250°-252°.

Workup

  1. temperatureunder reflux for 20 hours
  2. temperatureThe mixture was then cooled to 0°-4°
  3. customthe separated product collected
  4. filtrationfiltered
  5. filtrationfiltered
  6. washwashed with ether

Sources & evidence

ORD record
ord-d6c42c50deed43f3bc49f55f7fd4f6e2
Source dataset
uspto-grants-1981_01
Patent number
US04243666

Reaction notes

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