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

HRID 27146

Reaction equation

HRID 27146 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]([F: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]([F: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 20460532N-benzyloxycarbonyl-p-fluoroanilinoacetaldehyde diethyl acetal

Product 1

HCID 204605421-(N-benzyloxycarbonyl-p-fluoroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideYield 44.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-benzyloxycarbonyl-p-fluoroanilinoacetaldehyde 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). The mixture was then refluxed for 11 hours in a stream of nitrogen. In the course of the reaction, amounts of the above-mentioned acetal (0.6 g and 1.2 g) were added to the mixture after 4.5 hours and 6 hours, respectively, from the beginning of the reaction. The reaction mixture was concentrated to dryness and the residue was washed with ether and dissolved in water. The solution was washed with ether and concentrated to dryness to give amorphous 1-(N-benzyloxycarbonyl-p-fluoroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (2.7 g), mp 122° C. (dec.).

Workup

  1. temperatureThe mixture was then refluxed for 11 hours in a stream of nitrogen
  2. additionwere added to the mixture after 4.5 hours and 6 hours
  3. customrespectively, from the beginning of the reaction
  4. concentrationThe reaction mixture was concentrated to dryness
  5. washthe residue was washed with ether
  6. dissolutiondissolved in water
  7. washThe solution was washed with ether
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5ff7cb659ce54ae3ac8a4d37277a9d40
Source dataset
uspto-grants-1980_09
Patent number
US04220647

Linked notes

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