Dopamine Hydrochloride → HCID 4256496, compound

HRID 972639Notes

Reaction equation

HRID 972639 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][C:9]([OH:10])=[C:7]([OH:8])[CH:6]=1.[CH:13]1([C:16](Cl)=[O:17])[CH2:15][CH2:14]1>N1C=CC=CC=1>[OH:8][C:7]1[CH:6]=[C:5]([CH2:4][CH2:3][NH:2][C:16]([CH:13]2[CH2:15][CH2:14]2)=[O:17])[CH:12]=[CH:11][C:9]=1[OH:10]

Participants

4

Reactant 2

HCID 65340Dopamine HydrochlorideHCID 77637Cyclopropanecarbonyl chloride

Product 1

HCID 4256496HCID 4256496, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Dissolve 15.0 g. of dopamine hydrochloride in 200 ml. of pyridine. Add with stirring 24.96 g. of cyclopropane-carboxylic acid chloride portionwise over a 2-hour period at room temperature. Stir at room temperature overnight. Add methanol (200 ml.), water (75 ml.) and concentrate ammonium hydroxide solution (50 ml.) to the reaction mixture and allow the clear solution to stand for 5 hours at room temperature. Pour the solution into 2 liters of of 2N hydrochloric acid and ice with vigorous agitation. Extract the oily precipitate with ethyl acetate. Wash the extract with saturated aqueous sodium bicarbonate solution, dry over sodium sulfate and evaporate to a residue. Dissolve the residue from ethyl acetate-ethyl ether and crystallize to obtain the title compound, m.p. 174.5°-176° C.

Workup

  1. dissolutionDissolve 15.0 g
  2. additionAdd
  3. stirringStir at room temperature overnight
  4. concentrationAdd methanol (200 ml.), water (75 ml.) and concentrate ammonium hydroxide solution (50 ml.) to the reaction mixture
  5. additionPour the solution into 2 liters of of 2N hydrochloric acid and ice with vigorous agitation
  6. extractionExtract the oily precipitate with ethyl acetate
  7. washWash the
  8. extractionextract with saturated aqueous sodium bicarbonate solution
  9. dry with materialdry over sodium sulfate
  10. customevaporate to a residue
  11. dissolutionDissolve the residue from ethyl acetate-ethyl ether
  12. customcrystallize

Sources & evidence

ORD record
ord-b824dcd8a28448e2b360cdca4376f0bc
Source dataset
uspto-grants-1977_10
Patent number
US04053509

Reaction notes

Loading…