Potassium Carbonate → HCID 13135943, compound

HRID 2290441Notes

Reaction equation

HRID 2290441 reaction equation
[N:1]1([C:7]2[CH:17]=[CH:16][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)=[O:27]>C(#N)C>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([C:26](=[O:27])[CH2:25][N:4]2[CH2:3][CH2:2][N:1]([C:7]3[CH:8]=[CH:9][C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:16][CH:17]=3)[CH2:6][CH2:5]2)=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68303p-Chlorophenacyl bromideHCID 2761178Ethyl 4-(piperazin-1-yl)benzoate

Product 1

HCID 13135943HCID 13135943, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 11.7 g. (50 mmole) ethyl 4-(piperazin-1-yl)-benzoate, 13.8 g. (0.1 mole) powdered anhydrous potassium carbonate, 125 ml. acetonitrile and 11.7 g. (50 mmole) 2-bromo-4'-chloroacetophenone (p-chlorophenacyl bromide) is stirred for 20 hours at 20° C. The reaction mixture is then suction filtered and the filter cake is washed with acetone. The combined organic phases are evaporated to dryness in a vacuum to give 15.4 g. (80% of theory) of crude product. After recrystallisation from ethyl acetate, there are obtained 9.8 g. (51% of theory) of pure product; m.p. 152°-153° C. and from the mother liquor a further 1.4 g. (7% of theory) (m.p. 150°-152° C.) of product are obtained.

Workup

  1. additionA mixture of 11.7 g
  2. filtrationsuction filtered
  3. washthe filter cake is washed with acetone
  4. customThe combined organic phases are evaporated to dryness in a vacuum
  5. customto give 15.4 g
  6. customAfter recrystallisation from ethyl acetate, there
  7. customare obtained 9.8 g

Sources & evidence

ORD record
ord-4487bf76d6b4482c9bf8f5a3b439f235
Source dataset
uspto-grants-1986_10
Patent number
US04616086

Reaction notes

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