Dimethylformamide → N-(1-Ethyl-3-piperidyl)-4-(8-trifluoromethyl-4-quinolylamino)benzamide

HRID 2198487

Reaction equation

HRID 2198487 reaction equation
O.Cl.[F:3][C:4]([F:26])([F:25])[C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[N:13]=[CH:12][CH:11]=[C:10]2[NH:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=1.CN(C)C=O.[NH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][N:35]([CH2:39][CH3:40])[CH2:34]1.C(=O)([O-])[O-].[Na+].[Na+]>S(Cl)(Cl)=O.C(Cl)(Cl)Cl.O>[CH2:39]([N:35]1[CH2:36][CH2:37][CH2:38][CH:33]([NH:32][C:20](=[O:21])[C:19]2[CH:18]=[CH:17][C:16]([NH:15][C:10]3[C:9]4[C:14](=[C:5]([C:4]([F:25])([F:26])[F:3])[CH:6]=[CH:7][CH:8]=4)[N:13]=[CH:12][CH:11]=3)=[CH:24][CH:23]=2)[CH2:34]1)[CH3:40]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 980943-amino-N-ethylpiperidineHCID 705455024-(8-Trifluoromethyl-4-quinolylamino)benzoic acid hydrochloride monohydrate

Product 1

HCID 20520139N-(1-Ethyl-3-piperidyl)-4-(8-trifluoromethyl-4-quinolylamino)benzamideYield 37%

Reagents, catalysts & solvents 3

HCID 24386Thionyl ChlorideCatalystHCID 962WaterSolvent2×HCID 6212ChloroformSolvent

Procedure

11.6 Grams (0.03 mole) of 4-(8-trifluoromethyl-4-quinolylamino)benzoic acid hydrochloride monohydrate were refluxed in thionyl chloride containing a few drops of dimethyl formamide for one hour. The thionyl chloride was evaporated and 50 milliliters of benzene were added and evaporated. The resulting acid chloride hydrochloride was added in portions with stirring to a cooled mixture of 3.84 grams (0.03 mole) of 3-amino-1-ethylpiperidine in 80 milliliters of chloroform and 31.8 grams (0.3 mole) of sodium carbonate in 100 milliliters of water. The product began to precipitate almost at once, and the mixture was stirred vigorously for two hours, and allowed to stand overnight. Filtration gave a solid which was stirred in water, collected and dried. The resulting solid was dissolved in an ethanol:chloroform mixture and chromatographed on an alumine column made up in chloroform. Elution with chloroform gave 4.9 grams (37%) of title compound as a pale yellow solid, melting point 177°-178° C.

Workup

  1. customThe thionyl chloride was evaporated
  2. addition50 milliliters of benzene were added
  3. customevaporated
  4. additionThe resulting acid chloride hydrochloride was added in portions
  5. customto precipitate almost at once, and the mixture
  6. waitto stand overnight
  7. filtrationFiltration
  8. customgave a solid which
  9. customcollected
  10. customdried
  11. dissolutionThe resulting solid was dissolved in an ethanol
  12. customchloroform mixture and chromatographed on an alumine column
  13. washElution with chloroform

Sources & evidence

ORD record
ord-3328dc48c13a419da6dfce9ddbcfcab7
Source dataset
uspto-grants-1982_11
Patent number
US04357333

Linked notes

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