Hydrochloric Acid → HCID 21404983, compound

HRID 267868Notes

Reaction equation

HRID 267868 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.[C:13](Cl)(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15].[OH-].[NH4+].Cl>O.CO.N1C=CC=CC=1>[OH:8][C:7]1[CH:6]=[C:5]([CH2:4][CH2:3][NH:2][C:13](=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH:12]=[CH:11][C:9]=1[OH:10]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 62493Pivaloyl chlorideHCID 65340Dopamine Hydrochloride

Product 1

HCID 21404983HCID 21404983, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Dissolve 15.0 g. of dopamine hydrochloride in 200 ml. of pyridine. With stirring, add 28.8 g. of pivalyl chloride (α,α-dimethylpropionylchloride) portionwise over a 2-hour period at room temperature. Stir at room temperature overnight. Add methanol (200 ml.), water (75 ml.) and concentrated 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 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. Remove the last traces of ethyl acetate in vacuo and crystallize the product from a 9:1 toluene:ethanol mixture to obtain the title product m.p. 143.5°-146°C.

Workup

  1. dissolutionDissolve 15.0 g
  2. additionadd 28.8 g
  3. stirringStir at room temperature overnight
  4. extractionExtract the oily precipitate with ethyl acetate
  5. washWash the
  6. extractionextract with saturated aqueous sodium bicarbonate solution
  7. dry with materialdry over sodium sulfate
  8. customevaporate to a residue
  9. customRemove the last traces of ethyl acetate in vacuo
  10. customcrystallize the product from a 9:1 toluene

Sources & evidence

ORD record
ord-700e7352664b44a7a3f0fac6e163c2c7
Source dataset
uspto-grants-1976_03
Patent number
US03944675

Reaction notes

Loading…