Potassium Carbonate → HCID 54168561, compound

HRID 2290443Notes

Reaction equation

HRID 2290443 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][CH2:8]Cl)=[CH:4][CH:3]=1.[N:12]1([C:18]2[CH:30]=[CH:29][C:21]([C:22]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:23])=[CH:20][CH:19]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.CN(C)P(=O)(N(C)C)N(C)C.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][CH2:8][N:15]2[CH2:14][CH2:13][N:12]([C:18]3[CH:19]=[CH:20][C:21]([C:22]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:23])=[CH:29][CH:30]=3)[CH2:17][CH2:16]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 12679HexamethylphosphoramideHCID 1580057Butyl 4-piperazin-1-ylbenzoateHCID 53728250p-Chlorocinnamyl chloride

Product 1

HCID 54168561HCID 54168561, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 9.4 g. (50 mmole) 4-chlorocinnamyl chloride and 13.1 g. (50 mmole) n-butyl 4-(piperazin-1-yl)-benzoate in 40 ml. hexamethylphosphoric acid triamide is heated for 10 hours to 60° C., 6.9 g. (50 mmole) potassium carbonate are added thereto and stirring continued for 5 hours at 60° C. After cooling, the reaction mixture is diluted with the tenfold amount of water, the organic components are taken up in ethyl acetate and the dried ethyl acetate solution is evaporated. The residue is recrystallised from methanol to give 10.0 g. (48%) of desired product; m.p. 115°-117° C. The hydrochloride melts at 166°-168° C.

Workup

  1. additionA mixture of 9.4 g
  2. temperatureAfter cooling
  3. customthe dried ethyl acetate solution is evaporated
  4. customThe residue is recrystallised from methanol
  5. customto give 10.0 g

Sources & evidence

ORD record
ord-afc8be3f4f1b42c583ed625a7305db78
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

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