Triethylamine → HCID 21851294, compound

HRID 617170Notes

Reaction equation

HRID 617170 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.S(Cl)(Cl)=O.[NH2:18][CH2:19][CH2:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]2[C:36]3[C:31](=[CH:32][C:33]([O:39][CH3:40])=[C:34]([O:37][CH3:38])[CH:35]=3)[N:30]=[C:29]([Cl:41])[N:28]=2)[CH2:23][CH2:22]1.C(N(CC)CC)C>ClC(Cl)C.O>[Cl:41][C:29]1[N:28]=[C:27]([N:24]2[CH2:25][CH2:26][CH:21]([CH2:20][CH2:19][NH:18][C:7](=[O:9])[C:6]3[CH:10]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=3[N+:11]([O-:13])=[O:12])[CH2:22][CH2:23]2)[C:36]2[C:31](=[CH:32][C:33]([O:39][CH3:40])=[C:34]([O:37][CH3:38])[CH:35]=2)[N:30]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 183715-Methyl-2-nitrobenzoic acidHCID 24386Thionyl ChlorideHCID 21851266HCID 21851266, compound

Product 1

HCID 21851294HCID 21851294, compoundYield 136.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
100 °C

Procedure

To 2.5 g (11.8 mmol) of 5-methyl-2-nitrobenzoic acid was added 10 ml of thionyl chloride, followed by heating at 100° C. for 1.5 hours. The solvent was evaporated under reduced pressure, and 50 ml of dichloromethane was added to the residue to prepare Solution A. In dichloroethane was dissolved 2.5 g of 4-(2-aminoethyl)-1-(2-chloro-6,7-dimethoxy-4-quinazolinyl)piperidine obtained by the method described in Chem. Pharm. Bull., 38, 3014-3019 (1990) and the literature cited therein. To this solution was added 9.7 ml of triethylamine, and after stirring at room temperature, Solution A was added dropwise to the mixture. The resulting mixture was subjected to reaction at room temperature for 30 minutes and then was added dropwise to water, followed by extraction with dichloromethane. The organic layer was washed and dried, and the solvent was evaporated under reduced pressure. The residue was washed with a solvent mixture of ethanol and ether to give 5.0 g (yield: 83%) of Compound m as white crystals.

Workup

  1. customThe solvent was evaporated under reduced pressure, and 50 ml of dichloromethane
  2. additionwas added to the residue
  3. customto prepare Solution A
  4. customobtained by the method
  5. customThe resulting mixture was subjected to reaction at room temperature for 30 minutes
  6. extractionfollowed by extraction with dichloromethane
  7. washThe organic layer was washed
  8. customdried
  9. customthe solvent was evaporated under reduced pressure
  10. washThe residue was washed with a solvent mixture of ethanol and ether

Sources & evidence

ORD record
ord-bd98d1ae35c741248f5d7f1fd01e5285
Source dataset
uspto-grants-1999_09
Patent number
US05948784

Reaction notes

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