Potassium Carbonate → N-[3-(6-methyl-3-pyridyl)acryloyl]-4-(4-diphenylmethyl-1-piperazinyl)butylamine

HRID 868333Notes

Reaction equation

HRID 868333 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.C(Cl)(=O)C(C)(C)C.[C:20]1([CH:26]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[N:27]2[CH2:32][CH2:31][N:30]([CH2:33][CH2:34][CH2:35][CH2:36][NH2:37])[CH2:29][CH2:28]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(N(CC)CC)C>[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]([NH:37][CH2:36][CH2:35][CH2:34][CH2:33][N:30]2[CH2:31][CH2:32][N:27]([CH:26]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:28][CH2:29]2)=[O:12])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 62493Pivaloyl chlorideHCID 139569931-(4-Aminobutyl)-4-(diphenylmethyl)piperazineHCID 541408533-(6-Methyl-3-pyridyl)acrylic acid

Product 1

HCID 65933N-[3-(6-methyl-3-pyridyl)acryloyl]-4-(4-diphenylmethyl-1-piperazinyl)butylamineYield 72.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent4×HCID 8471TriethylamineSolvent

Conditions

Temperature
-5 °C

Procedure

To a suspension of 2.71 g of 3-(6-methyl-3-pyridyl)acrylic acid in 70 ml of dry tetrahydrofuran, a solution of 1.68 g of triethylamine in 5 ml of dry tetrahydrofuran is added at room temperature. The resulting solution is cooled to -5° C., and a solution of 2.0 g of pivaloyl chloride in 5 ml of dry tetrahydrofuran is added slowly. The mixture is stirred at the same temperature for 0.5 hour and cooled to -10° C., and a solution of 6.43 g of 4-(4-diphenylmethyl-1-piperazinyl)butylamine in 5 ml of dry tetrahydrofuran is added slowly. The mixture is stirred for 0.5 hour at between -10° C. and -5° C. and then at room temperature overnight. To the reaction mixture is added 50 ml of 10% aqueous potassium carbonate, and the resulting mixture is extracted with three 100-ml portions of ethyl acetate. The combined extracts are washed with water and dried over magnesium sulfate, and the solvent is distilled off. The residue is recrystallized from acetonitrile to give 5.63 g of the title compound, m.p. 129°-131° C.

Workup

  1. temperaturecooled to -10° C.
  2. stirringThe mixture is stirred for 0.5 hour at between -10° C. and -5° C.
  3. customat room temperature
  4. customovernight
  5. extractionthe resulting mixture is extracted with three 100-ml portions of ethyl acetate
  6. washThe combined extracts are washed with water
  7. dry with materialdried over magnesium sulfate
  8. distillationthe solvent is distilled off
  9. customThe residue is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-a404f031ff374c6fb9af01ee832418c5
Source dataset
uspto-grants-1988_10
Patent number
US04778796

Reaction notes

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