Benzocaine → Ethyl 4-(4-acetyl-3-hydroxy-2-propylbenzylamino)benzoate

HRID 275378Notes

Reaction equation

HRID 275378 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Cl)=[C:6]([CH2:12][CH2:13][CH3:14])[C:5]=1[OH:15])(=[O:3])[CH3:2].[NH2:16][C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:19][CH:18]=1>C(#N)C>[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH:16][C:17]2[CH:18]=[CH:19][C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][CH:27]=2)=[C:6]([CH2:12][CH2:13][CH3:14])[C:5]=1[OH:15])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2337Benzocaine2×HCID 137810224-Acetyl-3-hydroxy-2-propylbenzyl chloride

Product 1

HCID 15682682Ethyl 4-(4-acetyl-3-hydroxy-2-propylbenzylamino)benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6.8 g. of 4-acetyl-3-hydroxy-2propylbenzyl chloride and 14.9 g. of ethyl 4-aminobenzoate in 200 ml. of acetonitrile was heated to reflux for 48 hours. An additional 9.9 g. of ethyl 4aminobenzoate were added and the reaction was refluxed an additional 120 hours. The reaction mixture was cooled and concentrated in vacuo. The residue was dissolved in methylene chloride. The organic solution was washed first with a saturated sodium carbonate solution and then with water. The organic solution was then dried over sodium sulfate and evaporated to dryness. Chromatography of the residue afforded 7.4 g. of the desired title product. NMR.

Workup

  1. temperatureto reflux for 48 hours
  2. temperaturethe reaction was refluxed an additional 120 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in methylene chloride
  6. washThe organic solution was washed first with a saturated sodium carbonate solution
  7. dry with materialThe organic solution was then dried over sodium sulfate
  8. customevaporated to dryness
  9. customChromatography of the residue afforded 7.4 g

Sources & evidence

ORD record
ord-d36fc5e75a61410a94b108309b4d915b
Source dataset
uspto-grants-1995_02
Patent number
US05393768

Reaction notes

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