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

HRID 1586775

반응식

HRID 1586775 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f1a2c39fb1f247f7a437e4b783c83668
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05216018

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