Sodium hydride → 2-[4-(3-Trifluoromethylphenyl)-1-piperazinyl]-ethyl 3-(8-trifluoromethyl-4-quinolylamino)-2-thiophene-carboxylate

HRID 838947Notes

Reaction equation

HRID 838947 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[C:8]2[NH:13][C:14]1[CH:18]=[CH:17][S:16][C:15]=1[C:19]([O:21][CH3:22])=[O:20].[F:25][C:26]([F:43])([F:42])[C:27]1[CH:28]=[C:29]([N:33]2[CH2:38][CH2:37][N:36]([CH2:39]CO)[CH2:35][CH2:34]2)[CH:30]=[CH:31][CH:32]=1.[H-].[Na+]>C1(C)C=CC=CC=1>[F:24][C:2]([F:1])([F:23])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[C:8]2[NH:13][C:14]1[CH:18]=[CH:17][S:16][C:15]=1[C:19]([O:21][CH2:22][CH2:39][N:36]1[CH2:35][CH2:34][N:33]([C:29]2[CH:30]=[CH:31][CH:32]=[C:27]([C:26]([F:43])([F:25])[F:42])[CH:28]=2)[CH2:38][CH2:37]1)=[O:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2179944-(3-(Trifluoromethyl)phenyl)-1-piperazineethanolHCID 15916787Methyl 3-(8-trifluoromethyl-4-quinolylamino)-2-thiophene-carboxylate

Product 1

HCID 203254722-[4-(3-Trifluoromethylphenyl)-1-piperazinyl]-ethyl 3-(8-trifluoromethyl-4-quinolylamino)-2-thiophene-carboxylateYield 92.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 7 g of methyl 3-(8-trifluoromethyl-4-quinolylamino)-2-thiophene-carboxylate, 6.17 g of 4-(3-trifluoromethylphenyl)-1-piperazine-ethanol and 50 ml of anhydrous toluene was refluxed for an hour while passing condensed toluene through a column filled with siliporite and the mixture was cooled to 60° C. 150 mg of sodium hydride were added and the mixture was refluxed with stirring for 10 hours. The toluene was distilled and the residue was extracted with ether, washed with water and dried. The product was crystallized from methylene chloride to obtain 10.9 g of 2-[4-(3-trifluoromethylphenyl)-1-piperazinyl]-ethyl 3-(8-trifluoromethyl-4-quinolylamino)-2-thiophene-carboxylate.

Workup

  1. temperaturewas refluxed for an hour
  2. additionfilled with siliporite and the mixture
  3. temperaturethe mixture was refluxed
  4. distillationThe toluene was distilled
  5. extractionthe residue was extracted with ether
  6. washwashed with water
  7. customdried
  8. customThe product was crystallized from methylene chloride

Sources & evidence

ORD record
ord-205c3ad1d60c43f0b14cf8a091ab813a
Source dataset
uspto-grants-1978_06
Patent number
US04093724

Reaction notes

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