Water → HCID 20511279, compound

HRID 1284060Notes

Reaction equation

HRID 1284060 reaction equation
[ClH:1].[OH:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[OH:12])[CH2:6][CH2:7][NH2:8].C(O[CH:16](OCC)[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]=[CH2:28])=[CH:21][CH:20]=1)C.O>C(O)CCC.Cl>[ClH:1].[CH2:26]([O:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][CH2:17][CH:16]2[C:9]3[C:5](=[CH:4][C:3]([OH:2])=[C:11]([OH:12])[CH:10]=3)[CH2:6][CH2:7][NH:8]2)=[CH:20][CH:21]=1)[CH:27]=[CH2:28]

Participants

6

Reactant 3

HCID 962WaterHCID 65340Dopamine HydrochlorideHCID 20511270HCID 20511270, compound

Product 1

HCID 20511279HCID 20511279, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 2631-ButanolSolvent

Procedure

A solution of 3,4-dihydroxyphenethylamine hydrochloride (3.3 g) and (4-allyloxyphenoxy)acetaldehyde diethyl acetal (5.2 g) in a mixture of n-butanol (45 ml), water (12 ml) and concentrated hydrochloric acid (2 drops) was refluxed for 4 hours. After the reaction, the reaction mixture was concentrated to dryness. The residue was crystallized by adding acetone, and the crystals were recrystallized from a mixed solvent of 99% ethanol and ether to give 1-(4-allyloxyphenoxy)methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (6.0 g), mp 114° to 116°C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. customAfter the reaction
  3. concentrationthe reaction mixture was concentrated to dryness
  4. customThe residue was crystallized
  5. additionby adding acetone
  6. customthe crystals were recrystallized from a mixed solvent of 99% ethanol and ether

Sources & evidence

ORD record
ord-51520963a3e04d4785b254b61b6698b8
Source dataset
uspto-grants-1976_08
Patent number
US03978063

Reaction notes

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