Hydrochloric Acid → HCID 20323707, compound

HRID 839605Notes

Reaction equation

HRID 839605 reaction equation
C(O[CH:4](OCC)[CH2:5][NH:6][C:7]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=[N:9][N:8]=1)C.[ClH:21].[OH:22][C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][C:31]=1[OH:32])[CH2:26][CH2:27][NH2:28].C(O)C.Cl>O>[ClH:21].[C:12]1([N:11]2[C:7]([NH:6][CH2:5][CH:4]3[C:29]4[C:25](=[CH:24][C:23]([OH:22])=[C:31]([OH:32])[CH:30]=4)[CH2:26][CH2:27][NH:28]3)=[N:8][N:9]=[N:10]2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 65340Dopamine HydrochlorideHCID 85893808HCID 85893808, compound

Product 1

HCID 20323707HCID 20323707, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(1-phenyl-1H-tetrazol-5-yl)aminoacetaldehyde diethyl acetal (11 g.) and 3,4-dihydroxyphenethylamine hydrochloride (5.0 g.) were added to a mixture of ethanol (55 ml.) and water (20 ml.), and dissolved with heating and stirring. Conc. hydrochloric acid (6.0 g.) was added thereto and the mixture was refluxed for 8 hours. The reaction mixture was allowed to stand and the precipitated crystals were collected by filtration to give 1-(1-phenyl-1H-tetrazol-5-yl)aminomethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (5.9 g.). The crystals were recrystallized from a mixture of isopropyl alcohol and water to give pure crystals (4.2 g.), mp 236° to 241° C (dec.).

Workup

  1. dissolutiondissolved
  2. temperaturewith heating
  3. temperaturethe mixture was refluxed for 8 hours
  4. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-be15008aa31244469c75841649dbece8
Source dataset
uspto-grants-1978_06
Patent number
US04096263

Reaction notes

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