Triethylamine → HCID 20351360, compound

HRID 1448952Notes

Reaction equation

HRID 1448952 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.[CH3:17][S:18]([NH:21][CH2:22][CH2:23][CH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)(=[O:20])=[O:19].C(N(CC)CC)C>C(O)C>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][N:3]=[C:2]2[N:27]1[CH2:26][CH2:25][CH:24]([CH2:23][CH2:22][NH:21][S:18]([CH3:17])(=[O:20])=[O:19])[CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 20511180N-[2-(Piperidin-4-yl)ethyl]methanesulfonamide--hydrogen chloride (1/1)

Product 1

HCID 20351360HCID 20351360, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloro-6,7-dimethoxy quinazoline (1.1 g.), 4- (2-methanesulphonamidoethyl)piperidine hydrochloride (1.5 g.) and triethylamine (1.5 ml.) in ethanol (30 ml.) were heated together under reflux for 1.5 hours. The solution was then cooled to room temperature, concentrated in vacuo, suspended in water (70 ml.) and basified to pH 10 with 10% aqueous sodium carbonate solution. The mixture was extracted with chloroform (2×70 ml.), the extracts combined, dried (MgSO4), and taken to dryness in vacuo. The resultant pale yellow oil was triturated with ether (70 ml.) to give a white solid which was collected by filtration. Crystallization of this solid from ethanol yielded 6,7-dimethoxy-4-[4-(2-methanesulphonamidoethyl)-piperidino]quinazoline (1.7 g.), m.p. 162°-164° C.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. concentrationconcentrated in vacuo
  3. extractionThe mixture was extracted with chloroform (2×70 ml.)
  4. dry with materialdried (MgSO4)
  5. customThe resultant pale yellow oil was triturated with ether (70 ml.)
  6. customto give a white solid which
  7. filtrationwas collected by filtration
  8. customCrystallization of this solid from ethanol

Sources & evidence

ORD record
ord-2e8b6097bbd24989b8de0ccb073d3844
Source dataset
uspto-grants-1980_02
Patent number
US04188391

Reaction notes

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