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Allyl bromide → 2-Propenyl 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate

HRID 1973788
ノート
印刷プレビュー

反応式

HRID 1973788 の反応式
[C:1]1([NH:7][C:8]2([C:22]([OH:24])=[O:23])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na].CN(C)P(=O)(N(C)C)N(C)C.Br[CH2:38][CH:39]=[CH2:40]>O>[C:1]1([NH:7][C:8]2([C:22]([O:24][CH2:40][CH:39]=[CH2:38])=[O:23])[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:12][CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7841Allyl bromideHCID 12679HexamethylphosphoramideHCID 6162334-Piperidinecarboxylic acid, 4-(phenylamino)-1-(2-phenylethyl)-HCID 5360545Sodium

生成物 1

HCID 122981482-Propenyl 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate

試薬・触媒・溶媒 1

HCID 962Water
溶媒

反応条件

温度
110 °C

実験手順

A mixture of 10.4 parts of 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylic acid, sodium salt and 75 parts of hexamethylphosphoric triamide is stirred and heated to 110° C for a while. After cooling to 20° C, 3.63 parts of 3-bromo-1-propene are added dropwise. Upon completion, stirring is continued for 20 hours at room temperature. The reaction mixture is poured onto 150 parts of water and the product is extracted with methylbenzene. The extract is washed with water, filtered and evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 5% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The oily residue is crystallized from hexane, yielding 2-propenyl 4-(phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate; mp. 57.2° C.

後処理

  1. temperatureAfter cooling to 20° C
  2. stirringUpon completion, stirring
  3. extractionthe product is extracted with methylbenzene
  4. washThe extract is washed with water
  5. filtrationfiltered
  6. customevaporated
  7. customThe oily residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and 5% of methanol as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. customThe oily residue is crystallized from hexane

出典と根拠

ORDレコード
ord-039f306b59054020bfeff847c2e928e9
出典データセット
uspto-grants-1976_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US03998834

反応ノート

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