Diethyl Ether → N-(1-Ethyl-3-piperidyl)-2-(8-trifluoromethyl-4-quinolylamino)benzamide

HRID 2198484

Reaction equation

HRID 2198484 reaction equation
O.O.Cl.[F:4][C:5]([F:27])([F:26])[C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[N:14]=[CH:13][CH:12]=[C:11]2[NH:16][C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=O.[NH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][N:31]([CH2:35][CH3:36])[CH2:30]1.C(=O)([O-])[O-].[Na+].[Na+].CCOCC>S(Cl)(Cl)=O.C(Cl)(Cl)Cl.O>[CH2:35]([N:31]1[CH2:32][CH2:33][CH2:34][CH:29]([NH:28][C:19](=[O:21])[C:18]2[CH:22]=[CH:23][CH:24]=[CH:25][C:17]=2[NH:16][C:11]2[C:10]3[C:15](=[C:6]([C:5]([F:26])([F:27])[F:4])[CH:7]=[CH:8][CH:9]=3)[N:14]=[CH:13][CH:12]=2)[CH2:30]1)[CH3:36]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 980943-amino-N-ethylpiperidineHCID 705463792-(8-Trifluoromethyl-4-quinolylamino)benzoic acid hydrochloride dihydrate

Product 1

HCID 20520121N-(1-Ethyl-3-piperidyl)-2-(8-trifluoromethyl-4-quinolylamino)benzamideYield 63%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 24386Thionyl ChlorideSolvent

Procedure

11.5 Grams (0.0285 Mole) of 2-(8-trifluoromethyl-4-quinolylamino)benzoic acid hydrochloride dihydrate were refluxed in 80 milliliters of thionyl chloride for half an hour. A yellow solid precipitated. The thionyl chloride was evaporated off. The resulting acid chloride hydrochloride was added in portions with stirring to a cooled mixture of 3.84 grams (0.03 moles) of 3-amino-1-ethylpiperidine in 100 milliliters of chloroform and 31.8 grams (0.3 mole) of sodium carbonate in 100 milliliters of water. The mixture was stirred for one hour and allowed to stand overnight. The chloroform layer was separated and dried and the chloroform evaporated to give a nearly colourless solid. Trituration with ether gave a colourless solid which was recrystallized from methanol to give 7.9 grams (63% yield) of title compound, melting point 212° to 213° C.

Workup

  1. customA yellow solid precipitated
  2. customThe thionyl chloride was evaporated off
  3. additionThe resulting acid chloride hydrochloride was added in portions
  4. waitto stand overnight
  5. customThe chloroform layer was separated
  6. customdried
  7. customthe chloroform evaporated
  8. customto give a nearly colourless solid
  9. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-1430adf7fcdc446a94db511eb348b9a1
Source dataset
uspto-grants-1982_11
Patent number
US04357333

Linked notes

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