Potassium Carbonate → HCID 4742804, compound

HRID 1645805Notes

Reaction equation

HRID 1645805 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][OH:18])[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26](Cl)[C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[F:19][C:20]1[CH:21]=[CH:22][C:23]([CH:26]([C:27]2[CH:31]=[CH:30][S:29][CH:28]=2)[O:18][CH2:17][CH2:16][N:13]2[CH2:12][CH2:11][N:10]([CH2:9][CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:15][CH2:14]2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 782644HCID 782644, compoundHCID 57226181HCID 57226181, compound

Product 1

HCID 4742804HCID 4742804, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 1.1 g (0.0044 mol) 4-(3-phenylpropyl)-1-piperazine-ethanol, 1.0 g (0.0044 mol)(4-fluorophenyl)-(3-thienyl)methyl chloride (as prepared in step A), 1.22 g (0.0088 mol) potassium carbonate and 50 ml toluene was stirred and heated to reflux for 16 h. The reaction mixture was cooled, diluted with toluene and washed with water. The toluene layer was then extracted with 10% tartaric acid. The aqueous phase was separated and rendered basic by addition of 4N sodium hydroxide in excess and extracted with toluene. Evaporation gave the crude product as an oil, which was purified on a silica column (eluent was toluene/ethanol 2:1). The pure fraction was evaporated, redissolved in diethyl ether and treated with a solution of hydrogen chloride in ether. The precipitate was filtered off and recrystallized from isopropanol. The yield was 0.265 g (=12%) of the title compound as the dihydrochloride. M.p. 212°-15° C.

Workup

  1. temperatureheated
  2. temperatureto reflux for 16 h
  3. temperatureThe reaction mixture was cooled
  4. washwashed with water
  5. extractionThe toluene layer was then extracted with 10% tartaric acid
  6. customThe aqueous phase was separated
  7. additionrendered basic by addition of 4N sodium hydroxide in excess and
  8. extractionextracted with toluene
  9. customEvaporation

Sources & evidence

ORD record
ord-0e9465a088f14a7eb22035d2c7d90d4e
Source dataset
uspto-grants-1993_01
Patent number
US05177077

Reaction notes

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