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

HRID 838949Notes

Reaction equation

HRID 838949 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[NH:12][C:13]1[CH:17]=[CH:16][S:15][C:14]=1[C:18]([O:20][CH3:21])=[O:19].[F:22][C:23]([F:40])([F:39])[C:24]1[CH:25]=[C:26]([N:30]2[CH2:35][CH2:34][N:33]([CH2:36]CO)[CH2:32][CH2:31]2)[CH:27]=[CH:28][CH:29]=1.[H-].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[NH:12][C:13]1[CH:17]=[CH:16][S:15][C:14]=1[C:18]([O:20][CH2:21][CH2:36][N:33]1[CH2:32][CH2:31][N:30]([C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([C:23]([F:40])([F:22])[F:39])[CH:25]=2)[CH2:35][CH2:34]1)=[O:19]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2179944-(3-(Trifluoromethyl)phenyl)-1-piperazineethanolHCID 20325471Methyl 3-(8-chloro-4-quinolylamino)-2-thiophene-carboxylate

Product 1

HCID 203254752-[4-(3-Trifluoromethylphenyl)-1-piperazinyl]-ethyl 3-(8-chloro-4-quinolylamino)-2-thiophene-carboxylateYield 103.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of 6.37 g of the product of Step A, 6.17 g of 4-[3-trifluoromethylphenyl]-1-piperazine-ethanol and 50 ml of anhydrous toluene was refluxed for an hour while passing the condensed toluene through a column filled with siliporite and after cooling to 60° C, 150 mg of sodium hydride were added thereto. The mixture was refluxed with stirring for 16 hours and the toluene was distilled. The product was extracted with methylene chloride, washed with water and dried to obtain 11.6 g of 2-[4-(3-trifluoromethylphenyl)-1-piperazinyl]-ethyl 3-(8-chloro-4-quinolylamino)-2-thiophene-carboxylate.

Workup

  1. temperaturewas refluxed for an hour
  2. additionfilled with siliporite and
  3. temperatureThe mixture was refluxed
  4. distillationthe toluene was distilled
  5. extractionThe product was extracted with methylene chloride
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-4fc2706b79bb4c7393be003233f28348
Source dataset
uspto-grants-1978_06
Patent number
US04093724

Reaction notes

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