1-Butanol → HCID 131710330, compound

HRID 1284061Notes

Reaction equation

HRID 1284061 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 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 from a mixture solvent of methanol and ether

Sources & evidence

ORD record
ord-5b9263fecc2c40d8b341e873810d80f9
Source dataset
uspto-grants-1976_08
Patent number
US03978063

Reaction notes

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