Acetic Acid → 1-Carbamoyl-3-(4-fluorophenacyl)piperidine

HRID 1657832ノート

反応式

HRID 1657832 の反応式
[C:1]([N:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[O:11])[CH2:4]1)#[N:2].C(O)(=[O:21])C>Cl.O>[C:1]([N:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)=[O:11])[CH2:4]1)(=[O:21])[NH2:2]

参加物

5

反応物 2

HCID 176Acetic AcidHCID 215303571-Cyano-3-(4-fluorophenacyl)piperidine

生成物 1

HCID 215303701-Carbamoyl-3-(4-fluorophenacyl)piperidine

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒

実験手順

1-Cyano-3-(4-fluorophenacyl)piperidine (Example 19), 21.5 g, was dissolved in a mixture of 150 ml of glacial acetic acid, 30 ml of concentrated aqueous hydrochloric acid, and 70 ml of water. The resulting solution, under a nitrogen atmosphere, was heated on a steam-bath for 16 hours. The reaction solution was distilled under reduced pressure, the residue was diluted with water, and the resulting solution was made alkaline with 3 N sodium hydroxide. Upon extracting the alkaline aqueous solution with ethyl ether, solid precipitated and was isolated by filtration and washed with ether. The solid, 6.7 g, was recrystallized once from aqueous acetone and then four times from acetone/diethyl ether, to give 1-carbamoyl-3-(4-fluorophenacyl)piperidine, mp 136°-137.5°. The following elemental analysis was obtained:

後処理

  1. temperatureThe resulting solution, under a nitrogen atmosphere, was heated on a steam-bath for 16 hours
  2. distillationThe reaction solution was distilled under reduced pressure
  3. additionthe residue was diluted with water
  4. extractionUpon extracting the alkaline aqueous solution with ethyl ether, solid
  5. customprecipitated
  6. customwas isolated by filtration
  7. washwashed with ether
  8. customThe solid, 6.7 g, was recrystallized once from aqueous acetone

出典と根拠

ORDレコード
ord-d6a55369769a4cc0bede3e3e6cc97334
出典データセット
uspto-grants-1976_06
特許番号
US03962257

反応ノート

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