Potassium Carbonate → cis-2-(4-Bromophenethyl)-3a,4,7,7a-tetrahydroisoindoline

HRID 1586775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1586775
[CH2:1]1[C@@H:9]2[C@@H:4]([CH2:5][CH:6]=[CH:7][CH2:8]2)[CH2:3][NH:2]1.[Br:10][C:11]1[CH:19]=[CH:18][C:14]([CH2:15][CH2:16]Br)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>O.C1(C)C=CC=CC=1.CN(C)C=O>[Br:10][C:11]1[CH:19]=[CH:18][C:14]([CH2:15][CH2:16][N:2]2[CH2:3][C@H:4]3[C@H:9]([CH2:8][CH:7]=[CH:6][CH2:5]3)[CH2:1]2)=[CH:13][CH:12]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 110108254-Bromophenethyl bromideHCID 16765331cis-2,3,3a,4,7,7a-Hexahydro-1h-isoindole

Produkt 1

HCID 57058408cis-2-(4-Bromophenethyl)-3a,4,7,7a-tetrahydroisoindolineAusbeute 42,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 0.6 g of cis-3a,4,7,7a-tetrahydroisoindoline, 1.4 g of 4-bromophenethyl bromide, 1.0 g of potassium carbonate and 3 mL of dimethylformamide was stirred and heated in a 90° oil bath for 1 hour. Toluene (20 mL) and water (20 mL) were added and the aqueous layer was extracted with toluene. Addition of 10 mL of 10% hydrochloric acid to the toluene solution resulted in the formation of three layers. The two lower layers were made basic with aqueous sodium hydroxide solution. Extraction with methylene chloride gave 0.89 g of crude product which on short-path distillation gave 0.63 g of cis-2-(4-bromophenethyl)-3a,4,7,7a-tetrahydroisoindoline. 'H NMR (in CDCl3) δ7.4 (d, 2H); 7.0 (d, 2H); 5.8 (m, 2H); 3.0 (m, 2H); 2.6-2.8 (m, 4H); 2.4 (m, 2H); 2.1-2.3 (m, 4H) and 1.9 (d, 2H). The fumarate had m.p. 166°-167° after crystallization from ethanol.

Aufarbeitung

  1. temperatureheated in a 90° oil bath for 1 hour
  2. extractionthe aqueous layer was extracted with toluene
  3. additionAddition of 10 mL of 10% hydrochloric acid to the toluene solution
  4. customresulted in the formation of three layers
  5. extractionExtraction with methylene chloride
  6. customgave 0.89 g of crude product which
  7. distillationon short-path distillation

Quellen und Nachweise

ORD-Eintrag
ord-f1a2c39fb1f247f7a437e4b783c83668
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05216018

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