Sodium Iodide → rac-cis-N-[4-(1,2,3a,4,5,9b-hexahydro-6-methoxy-3H-benzo[e]indol-3-yl)butyl]phthalimide

HRID 1109098노트

반응식

HRID 1109098 반응식
[CH3:1][O:2][C:3]1[C:15]2[CH2:14][CH2:13][C@H:12]3[C@H:8]([CH2:9][CH2:10][NH:11]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:25][CH2:26][CH2:27][CH2:28][N:29]1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39]>CC(CC)=O.O>[CH3:1][O:2][C:3]1[C:15]2[CH2:14][CH2:13][C@H:12]3[C@H:8]([CH2:9][CH2:10][N:11]3[CH2:25][CH2:26][CH2:27][CH2:28][N:29]3[C:33](=[O:34])[C:32]4=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]4[C:30]3=[O:39])[C:7]=2[CH:6]=[CH:5][CH:4]=1

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 101650127rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole

생성물 1

HCID 131718425rac-cis-N-[4-(1,2,3a,4,5,9b-hexahydro-6-methoxy-3H-benzo[e]indol-3-yl)butyl]phthalimide수율 103.8%

시약·촉매·용매 2

HCID 962Water용매HCID 6569Methyl Ethyl Ketone용매

실험 절차

A solution of 1.00 g (0.005 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole in 60 ml of ethyl methyl ketone was treated with 0.86 g (0.006 mol) of potassium carbonate, 0.29 g (0.002 mol) of sodium iodide and 1.40 g (0.005 mol) of N-(4-bromobutyl)phthalimide. The mixture was boiled under reflux for 24 hours and, after cooling, treated with water. The mixture was extracted with ethyl acetate, the extracts were dried with sodium sulphate and the solvent was distilled off in a vacuum. Chromatography over silica gel with methylene chloride/methanol 20:1 gave 2.10 g (quant.) of crude rac-cis-N-[4-(1,2,3a,4,5,9b-hexahydro-6-methoxy-3H-benzo[e]indol-3-yl)butyl]phthalimide as pale yellow crystals. A small sample was recrystallized from ethyl acetate/ether and then exhibited a m.p. of 103°-105°.

후처리

  1. temperatureunder reflux for 24 hours
  2. temperatureafter cooling
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe extracts were dried with sodium sulphate
  5. distillationthe solvent was distilled off in a vacuum

출처 및 근거

ORD 기록
ord-3638c977a65841a181cafc6bcc8c61e9
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05318966

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