Potassium Carbonate → Ethyl 4-[(4-cycloheptyl)butylamino]cinnamate

HRID 2166765Notes

Reaction equation

HRID 2166765 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.Br[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+].CN(C)P(N(C)C)(N(C)C)=O>O>[CH2:24]1[CH2:23][CH2:22][CH2:21][CH:20]([CH2:19][CH2:18][CH2:17][CH2:16][NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:13][CH:14]=2)[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12679HexamethylphosphoramideHCID 97826Ethyl 3-(4-aminophenyl)acrylateHCID 13131543(4-Bromobutyl)cycloheptane

Product 1

HCID 54335838Ethyl 4-[(4-cycloheptyl)butylamino]cinnamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl p-aminocinnamate, 5.9 g. 4-bromobutylcycloheptane and one equivalent of anhydrous powdered potassium carbonate in 50 ml. hexamethylphosphoramide is heated for 20 hours at 60° C. The mixture is then cooled, diluted with water and extracted with ether. The combined ether extracts are dried, filtered and evaporated. Crystallization from acetonitrile provides the title compound as white crystals.

Workup

  1. temperatureThe mixture is then cooled
  2. extractionextracted with ether
  3. dry with materialThe combined ether extracts are dried
  4. filtrationfiltered
  5. customevaporated
  6. customCrystallization from acetonitrile

Sources & evidence

ORD record
ord-d97b4f8732974947a373d425e4dce30a
Source dataset
uspto-grants-1983_06
Patent number
US04388459

Reaction notes

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