Azepindole → 1H,2H,3H,4H,5H,11H,11aH-[1,4]diazepino[1,2-a]indole

HRID 2057356ノート

反応式

HRID 2057356 の反応式
[CH2:1]1[C:7]2=[CH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[N:6]2[CH2:5][CH2:4][CH2:3][NH:2]1.B.C1COCC1>FC(F)(F)C(O)=O.O1CCCC1>[CH2:1]1[CH:7]2[CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[N:6]2[CH2:5][CH2:4][CH2:3][NH:2]1

参加物

5

反応物 2

HCID 33471AzepindoleHCID 2723981Borane;tetrahydrofuran

生成物 1

HCID 124246601H,2H,3H,4H,5H,11H,11aH-[1,4]diazepino[1,2-a]indole

試薬・触媒・溶媒 2

HCID 6422Trifluoroacetic acid溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

70 milligrams of 2,3,4,5-tetrahydro-1H-[1,4]-diazepino [1,2-a]indole (prepared as described in U.S. Pat. No. 3,867,374) was dissolved in 3 milliliters of trifluoroacetic acid and the mixture was stirred for 10 minutes under nitrogen. Thereafter, 1.5 milliliters of a 1 M solution of BH3.THF in tetrahydrofuran was added dropwise with stirring and the resulting mixture stirred for 40 minutes to obtain a 2,3,4,5,11,11a-hexahydro-1H-[1,4]-diazepino[1,2-a]indole product in the reaction mixture. Water (0.5 milliliter) then was added dropwise to the mixture cooled in an ice bath, followed by 10 percent NaOH until pH tested about 9 (pH test paper). The alkaline solution was extracted with methylene chloride and the methylene chloride solution washed with saturated sodium chloride solution and dried over potassium carbonate. The dried solution was filtered to remove the drying agent and evaporated in vacuo to obtain 60 milligrams (85 percent yield) of 2,3,4,5,11,11a-hexahydro-1H-[1,4]diazepino[ 1,2-a]indole product as an oil having NMR and mass spectra appropriate for the compound. The hydrochloride salt of the product melted 238°-240° C.

後処理

  1. stirringwith stirring
  2. stirringthe resulting mixture stirred for 40 minutes

出典と根拠

ORDレコード
ord-55e2565893a24ec7b41620e6e6330d09
出典データセット
uspto-grants-1980_07
特許番号
US04210590

反応ノート

読み込み中…