1-Butanol → HCID 131710330, compound

HRID 1658327Notes

Reaction equation

HRID 1658327 reaction equation
C(O)CCC.[ClH:6].[OH:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=1[OH:17])[CH2:11][CH2:12][NH2:13].C(O[CH:21](OCC)[CH2:22][S:23][C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)C>Cl.O>[ClH:6].[CH3:30][C:27]1[CH:28]=[CH:29][C:24]([S:23][CH2:22][CH:21]2[C:14]3[C:10](=[CH:9][C:8]([OH:7])=[C:16]([OH:17])[CH:15]=3)[CH2:11][CH2:12][NH:13]2)=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 2631-ButanolHCID 65340Dopamine HydrochlorideHCID 70153171-[(2,2-Diethoxyethyl)sulfanyl]-4-methylbenzene

Product 1

HCID 131710330HCID 131710330, compoundYield 106.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 962WaterSolvent

Procedure

To a mixture of n-butanol (10 ml), water (2.5 ml) and concentrated hydrochloric acid (1 drop) were added 3,4-dihydroxyphenethylamine hydrochloride (0.63 g) and (4-methylthiophenoxy)acetaldehyde diethyl acetal (1.0 g), and the mixture was refluxed for 5 hours. After the reaction, the reaction mixture was concentrated to dryness under reduced pressure. The residue was crystallized by adding acetone, and the crystals were recrystallized by adding acetone, and the crystals were recryatallized from a mixture solvent of methanol and ether to give 1-(4-methylthiophenoxy)methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (1.2 g), mp 270°C (dec.).

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. customAfter the reaction
  3. concentrationthe reaction mixture was concentrated to dryness under reduced pressure
  4. customThe residue was crystallized
  5. additionby adding acetone
  6. customthe crystals were recrystallized
  7. additionby adding acetone

Sources & evidence

ORD record
ord-7de35176a47c47d3b07429883a883ca5
Source dataset
uspto-grants-1976_06
Patent number
US03963725

Reaction notes

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