Benzocaine → Ethyl 4-[3-(trimethylsilyl)propylamino]benzoate

HRID 652016Notes

Reaction equation

HRID 652016 reaction equation
[CH3:1][Si:2]([CH3:8])([CH3:7])[CH2:3][CH2:4][CH2:5]Br.[NH2:9][C:10]1[CH:20]=[CH:19][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][CH:11]=1>CN(C)P(N(C)C)(N(C)C)=O>[CH3:1][Si:2]([CH3:8])([CH3:7])[CH2:3][CH2:4][CH2:5][NH:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 2337BenzocaineHCID 128458003-Bromopropyltrimethylsilane

Product 1

HCID 13884861Ethyl 4-[3-(trimethylsilyl)propylamino]benzoate

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 20 g. 3-(trimethylsilyl)propyl bromide and 33.9 g. ethyl 4-aminobenzoate in 75 ml. hexamethylphosphoramide was stirred at 100° for 18 hr. The cooled reaction was diluted with 100 ml. water, the layers were separated, and the aqueous layer was washed three times 100 ml. portions of methylene chloride. The combined organic solutions were washed with water and brine, dried with anhydrous magnesium sulfate, passed through a pad of hydrous magnesium silicate, and evaporated to 96 g. orange liquid. The liquid was dissolved into 100 ml. ethanol and the product was precipitated with 100 ml. water. The solid was filtered and dried. Crystallization from water-ethanol yielded the title compound as a white solid, m.p. 64°-66° C.

Workup

  1. customThe cooled reaction
  2. additionwas diluted with 100 ml
  3. customwater, the layers were separated
  4. washthe aqueous layer was washed three times 100 ml
  5. washThe combined organic solutions were washed with water and brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customevaporated to 96 g
  8. dissolutionThe liquid was dissolved into 100 ml
  9. customethanol and the product was precipitated with 100 ml
  10. filtrationThe solid was filtered
  11. customdried
  12. customCrystallization from water-ethanol

Sources & evidence

ORD record
ord-91cbab4506ef4d86b9ba3a4c19b0dea6
Source dataset
uspto-grants-1987_06
Patent number
US04670421

Reaction notes

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