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

HRID 1109159ノート

反応式

HRID 1109159 の反応式
[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][CH2:29][N:30]1[C:34](=[O:35])[C:33]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:32]2[C:31]1=[O:40]>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][CH2:29][N:30]3[C:31](=[O:40])[C:32]4=[CH:39][CH:38]=[CH:37][CH:36]=[C:33]4[C:34]3=[O:35])[C:7]=2[CH:6]=[CH:5][CH:4]=1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 136770N-(5-Bromopentyl)phthalimideHCID 101650127rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole

生成物 1

HCID 131718501rac-N-[5-(cis-1,2,3a, 4,5,9b-hexahydro-6-methoxy-3H-benzo[e]indol-3-yl)pentyl]phthalimide収率 95%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6569Methyl Ethyl Ketone溶媒

実験手順

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 1.50 g (0.005 mol) of N-(5-bromopentyl)phthalimide. The mixture was heated 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 1.97 g (95%) of rac-N-[5-(cis-1,2,3a, 4,5,9b-hexahydro-6-methoxy-3H-benzo[e]indol-3-yl)pentyl]phthalimide.

後処理

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

出典と根拠

ORDレコード
ord-9edceda276f247ce9578ef5d8adf2ba3
出典データセット
uspto-grants-1994_06
特許番号
US05318966

反応ノート

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