Benzylaniline → HCID 21514274, compound

HRID 1605090Notes

Reaction equation

HRID 1605090 reaction equation
[C:1]1([NH:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC[O:17][C:18]([CH:20]1[C:25](=O)[CH:24](Br)[CH2:23][CH2:22][CH2:21]1)=[O:19]>O.[Cl-].[Zn+2].[Cl-]>[CH2:8]([N:7]1[C:22]2[CH2:23][CH2:24][CH2:25][CH:20]([C:18]([OH:19])=[O:17])[C:21]=2[C:2]2[C:1]1=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 66028BenzylanilineHCID 121765Ethyl 3-bromo-2-oxocyclohexanecarboxylate

Product 1

HCID 21514274HCID 21514274, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 962WaterSolvent

Procedure

A mixture of 53 g. of phenylbenzylamine and 30 g. of ethyl 6-bromocyclohexanone-2-carboxylate was maintained in a nitrogen atmosphere at 35° C. for several days. Fused powdered zinc chloride (48 g.) was added and the mixture was heated at 125°-130°C. for 11/2 hours. The cooled mixture was slurried in water and extracted with ether. The ether extract was washed with 5% hydrochloric acid and water, dried, and evaporated to dryness to give 38.5 g. crude ethyl ester of the title compound which was treated with a solution of 48 g. potassium hydroxide in 200 ml. water and 200 ml. ethyl alcohol at reflux temperature for three hours. The solution was evaporated to dryness under reduced pressure, the resulting residue was dissolved in water and the aqueous solution was extracted with ether and acidified with 10% hydrochloric acid. The resulting solids were collected and dried to give 27.4 g. of the title compound; m.p. 212°-215°C. (tetrahydrofuran-pentane).

Workup

  1. additionA mixture of 53 g
  2. temperaturethe mixture was heated at 125°-130°C. for 11/2 hours
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with 5% hydrochloric acid and water
  6. customdried
  7. customevaporated to dryness
  8. customto give 38.5 g

Sources & evidence

ORD record
ord-4f6de0bd001d4452a12f5522fd6c2c73
Source dataset
uspto-grants-1976_04
Patent number
US03948939

Reaction notes

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