Triethylamine → 2-[4-(3,4-Methylenedioxycinnamoyl)-piperazin-1-yl]-4-amino-6,7-dimethoxyquinazoline

HRID 1449160Notes

Reaction equation

HRID 1449160 reaction equation
[CH2:1]1[O:14][C:13]2[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=O)=[CH:4][C:3]=2[O:2]1.C(N(CC)CC)C.C(Cl)(=O)OCC.Cl.[N:29]1([C:35]2[N:44]=[C:43]([NH2:45])[C:42]3[C:37](=[CH:38][C:39]([O:48][CH3:49])=[C:40]([O:46][CH3:47])[CH:41]=3)[N:36]=2)[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1>O.C(OCC)(=O)C>[CH2:1]1[O:14][C:13]2[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([N:32]3[CH2:33][CH2:34][N:29]([C:35]4[N:44]=[C:43]([NH2:45])[C:42]5[C:37](=[CH:38][C:39]([O:48][CH3:49])=[C:40]([O:46][CH3:47])[CH:41]=5)[N:36]=4)[CH2:30][CH2:31]3)=[O:10])=[CH:4][C:3]=2[O:2]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 169173-(1,3-Benzodioxol-5-yl)prop-2-enoic acidHCID 204738332-Piperazine-4-amino-6,7-dimethoxyquinazoline hydrochloride

Product 1

HCID 537467432-[4-(3,4-Methylenedioxycinnamoyl)-piperazin-1-yl]-4-amino-6,7-dimethoxyquinazoline

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 346 mg. of 3,4-methylenedioxycinnamic acid and 364 mg. of triethylamine in 20 ml. of ethyl acetate were added under ice-cooling 195 mg. of ethyl chlorocarbonate and the resulting mixture was then stirred for 4 hours. Then, 543 mg. of 2-(piperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline.hydrochloride were added thereto and the resulting mixture was stirred at room temperature overnight. After 50 ml. of water were added, the precipitate thus separated was recovered by filtration. The resulting crystalline substance was recrystallized from ethanol to give 320 mg. of the desired product as the hydrochloride.

Workup

  1. temperaturecooling 195 mg
  2. customthe precipitate thus separated
  3. filtrationwas recovered by filtration
  4. customThe resulting crystalline substance was recrystallized from ethanol
  5. customto give 320 mg

Sources & evidence

ORD record
ord-6527e5e8b3a54e1faca099a64fd1412d
Source dataset
uspto-grants-1980_02
Patent number
US04189484

Reaction notes

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