Hydrochloric Acid → HCID 20511278, compound

HRID 1658329Notes

Reaction equation

HRID 1658329 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][N:22]=[CH:21][CH:20]=1)C.Cl>C(O)CCC>[ClH:1].[ClH:1].[N: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

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 65340Dopamine HydrochlorideHCID 20511268HCID 20511268, compound

Product 1

HCID 20511278HCID 20511278, compoundYield 215.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

A mixture of 3,4-dihydroxyphenethylamine hydrochloride (2.4 g), (4-pyridyl)oxyacetaldehyde diethyl acetal (3.7 g), n-butanol (40 ml) and 1N-hydrochloric acid (20 ml) was refluxed for 15 hours under stirring. After the reaction, n-butanol was distilled off from the reaction mixture under reduced pressure. The residue was dissolved in water, and the solution was washed twice with chloroform and once with ether. The aqueous layer was concentrated, and the oily residue was allowed to stand to give crystals of 1-(4-pyridyl)oxymethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride (4.7 g). The product was recrystallized from aqueous methanol to give needles, mp 250° to 255°C (dec.).

Workup

  1. temperaturewas refluxed for 15 hours
  2. distillationwas distilled off from the reaction mixture under reduced pressure
  3. dissolutionThe residue was dissolved in water
  4. washthe solution was washed twice with chloroform and once with ether
  5. concentrationThe aqueous layer was concentrated

Sources & evidence

ORD record
ord-5d786a57e60b4491929c710c4e97a3df
Source dataset
uspto-grants-1976_06
Patent number
US03963725

Reaction notes

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