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

HRID 1586775ノート

反応式

HRID 1586775 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f1a2c39fb1f247f7a437e4b783c83668
出典データセット
uspto-grants-1993_06
特許番号
US05216018

反応ノート

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