1-Butanol → 1-(N,N-diphenylaminomethyl)6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 543728Notes

Reaction equation

HRID 543728 reaction equation
C(O[CH:4](OCC)[CH2:5][N:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[ClH:22].[OH:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[OH:33])[CH2:27][CH2:28][NH2:29].C(O)CCC>Cl.O>[ClH:22].[C:13]1([N:6]([CH2:5][CH:4]2[C:30]3[C:26](=[CH:25][C:24]([OH:23])=[C:32]([OH:33])[CH:31]=3)[CH2:27][CH2:28][NH:29]2)[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 2631-ButanolHCID 65340Dopamine HydrochlorideHCID 12913315N,N-diphenylaminoacetaldehyde diethyl acetal

Product 1

HCID 705061331-(N,N-diphenylaminomethyl)6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideYield 35.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Procedure

N,N-diphenylaminoacetaldehyde diethyl acetal (3.5 g) and 3,4-dihydroxyphenethylamine hydrochloride (2.1 g) were added to a mixture of n-butyl alcohol (35 ml), water (5 ml) and conc. hydrochloric acid (2 drops) and then the mixture was refluxed for 6.5 hours in a stream of nitrogen. The reaction mixture was concentrated to dryness and the residue was washed with acetone and collected by filtration to recover the starting material, 3,4-dihydroxyphenethylamine (1.2 g). The filtrate was concentrated to give 1-(N,N-diphenylaminomethyl)6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.5 g), oil.

Workup

  1. temperaturethe mixture was refluxed for 6.5 hours in a stream of nitrogen
  2. concentrationThe reaction mixture was concentrated to dryness
  3. washthe residue was washed with acetone
  4. filtrationcollected by filtration
  5. customto recover the starting material, 3,4-dihydroxyphenethylamine (1.2 g)
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-410f2a402a2149fa87576ed501948d3e
Source dataset
uspto-grants-1984_05
Patent number
US04447436

Reaction notes

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