Triethylamine → 1-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinone

HRID 1414576Notes

Reaction equation

HRID 1414576 reaction equation
Cl[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]=[CH:4][N:3]=1.Cl.C1O[C:20]2([CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[O:19]C1.C(N(CC)CC)C.C(=O)([O-])[O-].[Na+].[Na+]>Cl.C(O)C>[O:19]=[C:20]1[CH2:25][CH2:24][N:23]([C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=3)[N:5]=[CH:4][N:3]=2)[CH2:22][CH2:21]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 162187951,4-Dioxa-8-azaspiro[4.5]decane--hydrogen chloride (1/1)

Product 1

HCID 147388231-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinoneYield 98%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

4-Chloro-6,7-dimethoxyquinazoline (30 g), 4-piperidone ethylene ketal hydrochloride (25 g), triethylamine (35 g) and ethanol (250 ml.) were refluxed together for 3 hours. Aqueous sodium carbonate was added followed by extraction with chloroform after which the chloroform extract was dried and evaporated in vacuo to give an oil. The oil was redissolved in aqueous hydrochloric acid (1.5N, 200 ml.) and refluxed for 2 hours followed by cooling, basification (Na2CO3 10% soln) and extraction into chlororform. Evaporation of the dried chloroform extract gave 4-(4-oxo-piperidino)-6,7-dimethoxyquinazoline (37.6 g) m.p. 176°-8° C.

Workup

  1. extractionfollowed by extraction with chloroform after which the chloroform
  2. extractionextract
  3. customwas dried
  4. customevaporated in vacuo
  5. customto give an oil
  6. temperaturerefluxed for 2 hours
  7. temperatureby cooling
  8. extractionbasification (Na2CO3 10% soln) and extraction into chlororform
  9. customEvaporation of the dried chloroform
  10. extractionextract

Sources & evidence

ORD record
ord-074f683bb77c4dde8950488fef0c78a2
Source dataset
uspto-grants-1977_01
Patent number
US04001422

Reaction notes

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