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

HRID 27149

Reaktionsgleichung

Reaktionsgleichung von HRID 27149
C(O[CH:4](OCC)[CH2:5][N:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)C.Cl.[OH:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[OH:33])[CH2:27][CH2:28][NH2:29].C(O)CCC.Cl>O>[ClH:13].[CH2:17]([O:16][C:14]([N:6]([CH2:5][CH:4]1[C:30]2[C:26](=[CH:25][C:24]([OH:23])=[C:32]([OH:33])[CH:31]=2)[CH2:27][CH2:28][NH:29]1)[C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1)=[O:15])[CH3:18]

Komponenten

6

Edukt 4

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 65340Dopamine HydrochlorideHCID 20460556N-ethoxycarbonyl-p-chloroanilinoacetaldehyde diethyl acetal

Produkt 1

HCID 204605721-(N-ethoxycarbonyl-p-chloroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

N-ethoxycarbonyl-p-chloroanilinoacetaldehyde diethyl acetal (3.0 g) and 3,4-dihydroxyphenethylamine hydrochloride (1.5 g) were added to a mixture of n-butyl alcohol (30 ml), water (5 ml) and 10% hydrochloric acid (0.5 ml), and then the mixture was refluxed for 4 hours in a stream of nitrogen. Above mentioned acetal (0.8 g) was further added to the mixture and the resultant mixture was refluxed for 4 hours. The solvent was distilled off from the reaction mixture and the residue was washed with ethyl acetate and then recrystallized from water to give 1-(N-ethoxycarbonyl-p-chloroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride, mp 208° to 210° C. and mp 214° to 215° C. Analysis: Calcd. for C19H21N2O4Cl.HCl.3/10H2O: C 54.50, H 5.44, N 6.69, Cl 16.93. Measured: C 54.29, H 5.57, N 6.70, Cl 16.69.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 4 hours in a stream of nitrogen
  2. additionwas further added to the mixture
  3. distillationThe solvent was distilled off from the reaction mixture
  4. washthe residue was washed with ethyl acetate
  5. customrecrystallized from water

Quellen und Nachweise

ORD-Eintrag
ord-690f05e8f4c04db7ac3665b77d3a8ce2
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04220647

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