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

HRID 1654658Notes

Reaction equation

HRID 1654658 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

HCID 57058408cis-2-(4-Bromophenethyl)-3a,4,7,7a-tetrahydroisoindolineYield 42.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

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. Anal. Calcd. for C20H24BrNO4 : C, 56.88; H, 5.73; N, 3.32 Found: C, 56.91; H, 5.64; N, 3.21

Workup

  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

Sources & evidence

ORD record
ord-d1e87fdd38d5407da323612de74585ed
Source dataset
uspto-grants-1995_04
Patent number
US05409929

Reaction notes

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