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

HRID 27145

Reaction equation

HRID 27145 reaction equation
C(O[CH:4](OCC)[CH2:5][N:6]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)C.[ClH:27].[OH:28][C:29]1[CH:30]=[C:31]([CH:35]=[CH:36][C:37]=1[OH:38])[CH2:32][CH2:33][NH2:34].C(O)CCC>O>[ClH:27].[CH2:17]([O:16][C:14]([N:6]([CH2:5][CH:4]1[C:35]2[C:31](=[CH:30][C:29]([OH:28])=[C:37]([OH:38])[CH:36]=2)[CH2:32][CH2:33][NH:34]1)[C:7]1[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][CH:12]=1)=[O:15])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 2631-ButanolHCID 65340Dopamine HydrochlorideHCID 20460580N-benzyloxycarbonyl-p-toluidinoacetaldehyde diethyl acetal

Product 1

HCID 204605901-(N-benzyloxycarbonyl-p-toluidinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideYield 63.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-benzyloxycarbonyl-p-toluidinoacetaldehyde diethyl acetal (6 g) and 3,4-dihydroxyphenethylamine hydrochloride (2.5 g) were added to a mixture of n-butyl alcohol (60 ml) and water (8.5 ml) and then the mixture was refluxed for 9.5 hours in a stream of nitrogen. In the course of the reaction, the above-mentioned acetal (0.6 g) was twice added to the mixture, after 5 hours and after 7.5 hours from the beginning of the reaction. The reaction mixture was concentrated and the residue was washed with ether and dissolved in hot water (300 ml). After the insoluble material was filtered off, the filtrate was washed with ethyl acetate and treated with activated charcoal. The aqueous layer was concentrated to dryness to give amorphous 1-(N-benzyloxycarbonyl-p-toluidinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (3.8 g), mp 125° C. (dec).

Workup

  1. temperaturethe mixture was refluxed for 9.5 hours in a stream of nitrogen
  2. customIn the course of the reaction
  3. concentrationThe reaction mixture was concentrated
  4. washthe residue was washed with ether
  5. dissolutiondissolved in hot water (300 ml)
  6. filtrationAfter the insoluble material was filtered off
  7. washthe filtrate was washed with ethyl acetate
  8. additiontreated with activated charcoal
  9. concentrationThe aqueous layer was concentrated to dryness

Sources & evidence

ORD record
ord-450ae31ddfe24a7bb4c2f7e67aba0817
Source dataset
uspto-grants-1980_09
Patent number
US04220647

Linked notes

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