Water → 4-(6,7-Dimethoxy-4-quinazolinyl)-N,N-diphenyl-1-piperazinecarboxamide

HRID 993157Notes

Reaction equation

HRID 993157 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(N(CC)CC)C.[C:28]1([N:34]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:35](Cl)=[O:36])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[CH2:16][CH2:17][N:18]([C:35]([N:34]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:36])[CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 65741N,N-Diphenylcarbamic chlorideHCID 27584846,7-Dimethoxy-4-piperazin-1-yl-quinazoline

Product 1

HCID 227076154-(6,7-Dimethoxy-4-quinazolinyl)-N,N-diphenyl-1-piperazinecarboxamideYield 99.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 10 ml of dimethylformamide was dissolved 400 mg (1.46 mmol) of 6,7-dimethoxy-4-piperazinylquinazoline obtained according to the method described in South African Patent No. 67 06512 (1968), and 1.02 ml (7.32 mmol) of triethylamine was added thereto. To the resulting mixture was added 406 mg (1.75 mmol) of diphenylcarbamoyl chloride, followed by overnight stirring at room temperature. After the reaction mixture was poured into water, the precipitated crystals were collected by filtration, followed by purification by silica gel column chromatography to give 680 mg of the desired compound as colorless crystals.

Workup

  1. customobtained
  2. filtrationthe precipitated crystals were collected by filtration
  3. customfollowed by purification by silica gel column chromatography

Sources & evidence

ORD record
ord-23867361934e497ea4b4dd8c413d865b
Source dataset
uspto-grants-2002_10
Patent number
US06472391B2

Reaction notes

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