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Hydrochloric Acid → 1-Aminomethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride

HRID 543738
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 543738
[ClH:1].C(OC([NH:12][CH2:13][CH:14]1[C:23]2[C:18](=[CH:19][C:20]([OH:25])=[C:21]([OH:24])[CH:22]=2)[CH2:17][CH2:16][NH:15]1)=O)C1C=CC=CC=1.Cl>C(O)(=O)C>[ClH:1].[ClH:1].[NH2:12][CH2:13][CH:14]1[C:23]2[C:18](=[CH:19][C:20]([OH:25])=[C:21]([OH:24])[CH:22]=2)[CH2:17][CH2:16][NH:15]1
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Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 204605221-(N-benzyloxycarbonylaminomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Produkt 1

HCID 128577221-Aminomethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochlorideAusbeute 61,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 1-(N-benzyloxycarbonylaminomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (5.3 g), conc. hydrochloric acid (6 ml) and acetic acid (6 ml) was refluxed for 1 hour and 20 minutes. The reaction mixture was cooled and concentrated under reduced pressure. The residue was crystallized by adding methanol and acetone. The crystals were collected by filtration, washed with a mixture of methanol and acetone and recrystallized twice from a mixture of water, methanol and acetone to give 1-aminomethyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline dihydrochloride (1.2 g), mp 142° to 147° C. (dec).

Aufarbeitung

  1. temperaturewas refluxed for 1 hour and 20 minutes
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was crystallized
  5. additionby adding methanol and acetone
  6. filtrationThe crystals were collected by filtration
  7. washwashed with a mixture of methanol and acetone
  8. customrecrystallized twice from a mixture of water, methanol and acetone

Quellen und Nachweise

ORD-Eintrag
ord-c3308f8261a0423da4562c4eaa563169
Quelldatensatz
uspto-grants-1984_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04447436

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