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Ethanol → 2-Benzyl-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 1953558
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1953558
[ClH:1].[N+:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][NH:11][CH2:12]2)=[CH:7][CH:6]=1)([O-:4])=[O:3].C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O)C>C(#N)C.CCOCC>[ClH:1].[CH2:21]([N:11]1[CH2:10][CH2:9][C:8]2[C:13](=[CH:14][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][CH:7]=2)[CH2:12]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 702EthanolHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 135216707-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

Produkt 1

HCID 232984082-Benzyl-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283
Diethyl Ether
Lösungsmittel
HCID 6342AcetonitrileLösungsmittel2×

Versuchsvorschrift

To a solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline monohydrochloride (2.50 g, 11.6mmol) and potassium carbonate (2.0 g) in acetonitrile (100 ml) was added benzyl bromide (2.22 g, 13.0 mmol) in acetonitrile (10 ml). The solution was stirred overnight and the solid was then removed by filtration. The solvent was removed in vacuo to give a solid which was partitioned between methylene chloride and water. The dried (MgSO4) organic phase was concentrated and the resulting oil was taken up in ethanol (50 ml). This solution was made acidic with hydrochloric acid in ethanol. The precipitate which formed had set up solid and an additional 150 ml of ethanol and 50 ml of ether was added. The solid was collected and air dried to give 2-benzyl-7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride as an off white solid (2.78 g (79%)), m.p. 256-8° C. (dec).

Aufarbeitung

  1. customthe solid was then removed by filtration
  2. customThe solvent was removed in vacuo
  3. customto give a solid which
  4. customwas partitioned between methylene chloride and water
  5. dry with materialThe dried (MgSO4) organic phase
  6. concentrationwas concentrated
  7. customThe precipitate which formed
  8. customThe solid was collected
  9. customair dried

Quellen und Nachweise

ORD-Eintrag
ord-fb31acabb41141c583808fcc17e4ef5b
Quelldatensatz
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06117898

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