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Sodium hydride → 2-(9-chloro-2,3,4,5-tetrahydro-3-methylazepino[4,5-b]indol-6(1H)-yl)-1-(4-methylpiperidin-1-yl)ethanone

HRID 1045595
ノート
印刷プレビュー

反応式

HRID 1045595 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[CH:11][C:10]2[NH:9][C:8]3[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17][C:7]=3[C:6]=2[CH:5]=1.Cl[CH2:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]1)=[O:22]>CCCCCC.C1COCC1>[Cl:3][C:4]1[CH:12]=[CH:11][C:10]2[N:9]([CH2:20][C:21]([N:23]3[CH2:28][CH2:27][CH:26]([CH3:29])[CH2:25][CH2:24]3)=[O:22])[C:8]3[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17][C:7]=3[C:6]=2[CH:5]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 41169262-Chloro-1-(4-methylpiperidin-1-yl)ethan-1-oneHCID 685585079-Chloro-3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole

生成物 1

HCID 593684162-(9-chloro-2,3,4,5-tetrahydro-3-methylazepino[4,5-b]indol-6(1H)-yl)-1-(4-methylpiperidin-1-yl)ethanone収率 59.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran
溶媒
2 回
HCID 8058Hexane溶媒

実験手順

The title compound was prepared by following general procedure 7. Sodium hydride (34 mg, 0.43 mmol) washed with hexane for removal of oil and dried under vacuum and taken in THF. To this solution 9-chloro-3-methyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.1 g, 0.43 mmol) in THF was added dropwise at 0° C. Then the reaction mixture was stirred for 0.5 h. The solution of 2-chloro-1-(4-methylpiperidin-1-yl)ethanone (89 mg, 0.51 mmol) in THF was added dropwise in reaction mixture. Then the reaction mixture was stirred at RT for 2 h. The reaction monitored by TLC. After completion of the reaction, the reaction mixture was quenched with ice water. THF was evaporated and aqueous layer was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The crude compound was washed with hexane and diethyl ether for removal of color impurities then recrystallized by using methanol to gives 95 mg of desired compound, which was stirred with ethanolic HCl to give the HCl salt of 2-(9-chloro-3-methyl-2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)-1-(4-methylpiperidin-1-yl)ethanone.

後処理

  1. customThe title compound was prepared
  2. customdried under vacuum
  3. stirringThen the reaction mixture was stirred at RT for 2 h
  4. customAfter completion of the reaction
  5. customthe reaction mixture was quenched with ice water
  6. customTHF was evaporated
  7. extractionaqueous layer was extracted with ethyl acetate
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. washThe crude compound was washed with hexane and diethyl ether for removal of color impurities
  10. customthen recrystallized

出典と根拠

ORDレコード
ord-be7f6ed2de7444c1a0e15a8f1f4f874b
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08569287B2

反応ノート

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