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Water → Methyl 4-[(ethoxycarbonyl)phenylamino]-1-(2-phenylethyl)-4-piperidinecarboxylate ethanedioate

HRID 1448344
ノート
印刷プレビュー

反応式

HRID 1448344 の反応式
Br[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:10]([O:12][C:13]([N:15]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:16]1([C:22]([O:24][CH3:25])=[O:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)=[O:14])[CH3:11].C(N(CC)CC)C.CN(C)C(=[O:43])C.[OH2:45]>>[C:22]([OH:24])(=[O:23])[C:16]([OH:43])=[O:45].[CH2:10]([O:12][C:13]([N:15]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:16]1([C:22]([O:24][CH3:25])=[O:23])[CH2:21][CH2:20][N:19]([CH2:2][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:18][CH2:17]1)=[O:14])[CH3:11]
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 5

HCID 962WaterHCID 7666Phenethyl bromideHCID 8471TriethylamineHCID 31374DimethylacetamideHCID 54241043Methyl 4-[(ethoxycarbonyl)phenylamino]-4-piperidinecarboxylate

生成物 1

HCID 86734319Methyl 4-[(ethoxycarbonyl)phenylamino]-1-(2-phenylethyl)-4-piperidinecarboxylate ethanedioate

反応条件

温度
70 °C

実験手順

A mixture of 7.73 parts of (2-bromoethyl)benzene, 11.7 parts of methyl 4-[(ethoxycarbonyl)phenylamino]-4-piperidinecarboxylate, 6.9 parts of N,N-diethylethanamine and 171 parts of N,N-dimethylacetamide is stirred for 3 hours at 70° C. The reaction mixture is cooled to room temperature and poured onto 600 parts of water. The product is extracted with 360 parts of benzene. The extract is washed three times with water, dried, filtered and evaporated. The residue is purified twice by column-chromatography over silica gel using first trichloromethane and then a mixture of trichloromethane and methanol (95:5) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is converted into the ethanedioate salt in 2-propanol. The salt is filtered off and boiled in 2-propanol. The product is filtered off and dried in vacuo at 120° C., yielding 5 parts of methyl 4-[(ethoxycarbonyl)phenylamino]-1-(2-phenylethyl)-4-piperidinecarboxylate ethanedioate; mp. 206.8° C.

後処理

  1. temperatureThe reaction mixture is cooled to room temperature
  2. extractionThe product is extracted with 360 parts of benzene
  3. washThe extract is washed three times with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified twice by column-chromatography over silica gel using first trichloromethane
  8. additiona mixture of trichloromethane and methanol (95:5) as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. filtrationThe salt is filtered off
  12. filtrationThe product is filtered off
  13. customdried in vacuo at 120° C.

出典と根拠

ORDレコード
ord-9651987b6d114f549ceb94573df2e8f3
出典データセット
uspto-grants-1979_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04179569

反応ノート

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