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Hydrochloric Acid → 2-[3-(4-benzylpiperidin-1-yl)-propyl]-2H-1,4-benzoxazine-3(4H)-one

HRID 1974471
ノート
印刷プレビュー

反応式

HRID 1974471 の反応式
Br[CH2:2][CH2:3][CH2:4][CH:5]1[C:10](=[O:11])[NH:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[O:6]1.NC1C=CC=CC=1O.BrC(CCCBr)C(Br)=O.[CH2:33]([CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.Cl>C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH2:33]([CH:40]1[CH2:45][CH2:44][N:43]([CH2:2][CH2:3][CH2:4][CH:5]2[C:10](=[O:11])[NH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[O:6]2)[CH2:42][CH2:41]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 58012-AminophenolHCID 317384-BenzylpiperidineHCID 111630822,5-dibromopentanoyl BromideHCID 143046582-(3-bromopropyl)-2H-1,4-benzoxazine-3(4H)-one

生成物 1

HCID 150279152-[3-(4-benzylpiperidin-1-yl)-propyl]-2H-1,4-benzoxazine-3(4H)-one

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8471Triethylamine溶媒

実験手順

5.6 g (=0.02 m) of 2-(3-bromopropyl)-2H-1,4-benzoxazine-3(4H)-one prepared analogously to Example 1B starting from 2-aminophenol and 2,5-dibromopentanoyl bromide, 3.86 g (=0.022 m) of 4-benzylpiperidine, and 4.05 g of triethylamine were successively introduced into 70 ml of toluene. The reaction mixture was heated at reflux for 7 hours with stirring. To work up the reaction mixture it was cooled, and 100 ml of aqueous 20% strength hydrochloric acid solution were added. An oily paste was formed which was separated, washed with toluene, and then suspended in a mixture of aqueous sodium bicarbonate solution and dichloromethane. The organic phase was separated, dried over sodium sulfate, and then the solvent was distilled off. The remaining oily residue was fractionated by column chromatography. The title compound obtained in this way was crystallized from 15 ml of ethyl acetate. 6 g of 2-[3-(4-benzylpiperidin-1-yl)-propyl]-2H-1,4-benzoxazine-3(4H)-one were obtained as white crystals having a melting point of 108° C.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 7 hours
  3. temperaturewas cooled
  4. customAn oily paste was formed which
  5. customwas separated
  6. washwashed with toluene
  7. additionsuspended in a mixture of aqueous sodium bicarbonate solution and dichloromethane
  8. customThe organic phase was separated
  9. dry with materialdried over sodium sulfate
  10. distillationthe solvent was distilled off

出典と根拠

ORDレコード
ord-29d724bbac01484490c24ad2a4686a96
出典データセット
uspto-grants-1994_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05283243

反応ノート

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