Hydrochloric Acid → HCID 54003055, compound

HRID 729012Notes

Reaction equation

HRID 729012 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[OH-].[K+].[O:12]1[CH2:24][CH:13]1[CH2:14][O:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]#[N:19]>C(O)C>[C:18]([C:17]1[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=1[O:15][CH2:14][CH:13]([OH:12])[CH2:24][NH:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])#[N:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 419889Ethyl 3-aminopropanoateHCID 126196712-(Oxiran-2-ylmethoxy)benzonitrile

Product 1

HCID 54003055HCID 54003055, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

15.36 g of the hydrochloride of ethyl 3-aminopropanoate and 6.2 g of potassium hydroxide were stirred in 150 ml of abs. ethanol until neutral reaction, ca 1 h. Under reflux was added 8.7 g of 2-(2,3-epoxypropoxy)benzonitrile in 125 ml of abs. ethanol. The mixture was refluxed for 8 h, filtered and evaporated. The residue was dissolved in ether, washed twice with water and extracted with 25 ml of 2-n hydrochloric acid. The aqueous phase was extracted with methylene chloride. The methylene chloride phase was dried over Na2SO4, filtered and evaporated to dryness. The hydrochloride of ethyl N-[3-(2-cyanophenoxy)-2-hydroxypropyl]-3-aminopropanoate crystallized. Yield 5.75 g. Melting point 120° C. (HCl). The structure was determined using NMR and equivalent weight.

Workup

  1. temperatureUnder reflux
  2. temperatureThe mixture was refluxed for 8 h
  3. filtrationfiltered
  4. customevaporated
  5. dissolutionThe residue was dissolved in ether
  6. washwashed twice with water
  7. extractionextracted with 25 ml of 2-n hydrochloric acid
  8. extractionThe aqueous phase was extracted with methylene chloride
  9. dry with materialThe methylene chloride phase was dried over Na2SO4
  10. filtrationfiltered
  11. customevaporated to dryness
  12. customThe hydrochloride of ethyl N-[3-(2-cyanophenoxy)-2-hydroxypropyl]-3-aminopropanoate crystallized

Sources & evidence

ORD record
ord-cc46c5ec84a14c2caee42c63827d47f9
Source dataset
uspto-grants-1991_09
Patent number
US05051446

Reaction notes

Loading…