Hydrochloric Acid → HCID 20506459, compound

HRID 354818Notes

Reaction equation

HRID 354818 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([O:15][CH3:16])[C:8]([O:13][CH3:14])=[C:9]([Cl:12])[CH:10]=2)[N:5]=[C:4](Cl)[N:3]=1.[CH2:18]([O:20][CH2:21][CH2:22][O:23][CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[CH3:19].C(N(CC)CC)C.Cl>C(O)CCC.C(O)C>[ClH:12].[CH2:18]([O:20][CH2:21][CH2:22][O:23][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:15][CH3:16])[C:8]([O:13][CH3:14])=[C:9]([Cl:12])[CH:10]=3)[N:5]=2)[CH2:26][CH2:25]1)[CH3:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 12920006HCID 12920006, compoundHCID 140223854-(2-Ethoxyethoxy)piperidine

Product 1

HCID 20506459HCID 20506459, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 702EthanolSolvent

Procedure

4-Amino-2,6-dichloro-7,8-dimethoxyquinazoline (4.9 g.), 4-(2-ethoxyethoxy)piperidine (3.2 g.) and triethylamine (10 ml.) in n-butanol (400 ml.) are heated at reflux overnight under an atmosphere of nitrogen. The mixture is then cooled, evaporated in vacuo, and the residue basified (aqueous Na2CO3) and extracted 3 times with chloroform. The combined chloroform extracts are evaporated and the residue chromatographed on neutral alumina to give the crude product which is converted to the hydrochloride salt by treatment with hydrogen chloride in ethanol to afford the title compound. C. By the above procedures the following compounds are similarly provided from the appropriate starting materials in each case.

Workup

  1. temperatureat reflux overnight under an atmosphere of nitrogen
  2. temperatureThe mixture is then cooled
  3. customevaporated in vacuo
  4. extractionextracted 3 times with chloroform
  5. customThe combined chloroform extracts are evaporated
  6. customthe residue chromatographed on neutral alumina
  7. customto give the crude product which

Sources & evidence

ORD record
ord-d6f6acc30cc44fcaa2478df6c63a6b86
Source dataset
uspto-grants-1983_03
Patent number
US04377581

Reaction notes

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