Dopamine Hydrochloride → HCID 20323709, compound

HRID 839608Notes

Reaction equation

HRID 839608 reaction equation
[ClH:1].[OH:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[OH:12])[CH2:6][CH2:7][NH2:8].C(O[CH:16](OCC)[CH2:17][NH:18][C:19]1[S:20][CH:21]=[N:22][N:23]=1)C>Cl.C(O)C.O>[ClH:1].[S:20]1[CH:21]=[N:22][N:23]=[C:19]1[NH:18][CH2:17][CH:16]1[C:9]2[C:5](=[CH:4][C:3]([OH:2])=[C:11]([OH:12])[CH:10]=2)[CH2:6][CH2:7][NH:8]1

Participants

6

Reactant 2

HCID 65340Dopamine HydrochlorideHCID 85893809HCID 85893809, compound

Product 1

HCID 20323709HCID 20323709, compoundYield 33.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Conc. hydrochloric acid (2 drops) was added to a solution of 3,4-dihydroxyphenethylamine hydrochloride (1.8 g.) and (1,3,4-thiadiazol-2-yl)aminoacetaldehyde diethyl acetal (3.1 g.) in a mixture of ethanol (60 ml) and water (15 ml.). The resulting mixture was refluxed for 18 hours. After cooling, the reaction mixture was allowed to stand at ambient temperature. Precipitating crystals were collected by filtration and washed with ethanol to give 1-(1,3,4-thiadiazol-2-yl)aminomethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.0 g.).

Workup

  1. temperatureThe resulting mixture was refluxed for 18 hours
  2. temperatureAfter cooling
  3. customto stand at ambient temperature
  4. customPrecipitating crystals
  5. filtrationwere collected by filtration
  6. washwashed with ethanol

Sources & evidence

ORD record
ord-f2fe07fdb34d4981996fab5a4f75ca78
Source dataset
uspto-grants-1978_06
Patent number
US04096263

Reaction notes

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