Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 2-Chloro-6,7-dimethoxy-4-quinazolinamine | HCID 90235 | — |
| Reactant | 4-(2-Ethoxyethoxy)piperidine | HCID 14022385 | — |
| Solvent | 1-Butanol | HCID 263 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 14022356 | HCID 14022356 | 45.9% |
Reaction Steps
4-Amino-2-chloro-6,7-dimethoxyquinazoline (4.3 g.), 4-(2-ethoxyethoxy)piperidine (3.2 g.) and triethylamine (10 ml.) in n-butanol (400 ml.) were heated at reflux overnight under an atmosphere of nitrogen. The mixture was then cooled, evaporated in vacuo, and the residue basified (aqueous Na2CO3) and extracted 3 times with chloroform. The combined chloroform extracts were evaporated and the residue chromatographed on neutral alumina (150 g., Grade I, deactivated with 5 ml water). Elution with chloroform gave the crude product (3.6 g.) which was converted to the hydrochloride salt by treatment with hydrogen chloride in ethanol. The hydrochloride was then recrystallized from ethanol/isopropanol to give 4-amino-6,7-dimethoxy-2-[4-(2-ethoxyethoxy)piperidino]quinazoline hydrochloride (3.4 g.), m.p. 219°-220° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04237138 |
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| Source dataset | uspto-grants-1980_12 |
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| ORD ID | ord-51b1d4af8f95421ea7e034b6a543f1b8 |
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| Source note | uspto-grants-1980_12 |
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