Lithium amide → 4-(4-Fluoro-2-methylphenyl)-1-(4-methylphenylsulfonyl)-4-piperidinecarbonitrile

HRID 1164357ノート

反応式

HRID 1164357 の反応式
Cl[CH2:2][CH2:3][N:4]([CH2:15][CH2:16]Cl)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:7])=[O:6].[F:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]#[N:27])=[C:21]([CH3:28])[CH:20]=1.[NH2-].[Li+]>CC1C=CC=CC=1>[F:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2([C:26]#[N:27])[CH2:16][CH2:15][N:4]([S:5]([C:8]3[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=3)(=[O:7])=[O:6])[CH2:3][CH2:2]2)=[C:21]([CH3:28])[CH:20]=1

参加物

5

反応物 3

HCID 24532Lithium amideHCID 96039N,N-bis(2-chloroethyl)-p-toluenesulphonamideHCID 38654692-(4-Fluoro-2-methylphenyl)acetonitrile

生成物 1

HCID 205118204-(4-Fluoro-2-methylphenyl)-1-(4-methylphenylsulfonyl)-4-piperidinecarbonitrile収率 72.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

A solution of 29.6 parts of N,N-bis(2-chloroethyl)-4-methylbenzenesulfonamide and 14.9 parts of 4-fluoro-2-methylbenzeneacetonitrile in 90 parts of methylbenzene is added dropwise to a solution of 5.6 parts of lithium amide in 270 parts of methylbenzene at about 90° C. Upon completion, the whole is heated to reflux and stirred overnight at reflux temperature. The reaction mixture is cooled, poured onto water and the layers are separated. The organic phase is dried, filtered and evaporated. The residue is crystallized from 2-propanol, yielding 27 parts (72.6%) of 4-(4-fluoro-2-methylphenyl)-1-(4-methylphenylsulfonyl)-4-piperidinecarbonitrile.

後処理

  1. temperatureUpon completion, the whole is heated
  2. temperatureto reflux
  3. temperatureat reflux temperature
  4. temperatureThe reaction mixture is cooled
  5. additionpoured onto water
  6. customthe layers are separated
  7. customThe organic phase is dried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is crystallized from 2-propanol

出典と根拠

ORDレコード
ord-0d4b8d3cefb5432fa8e36670d0c73f4f
出典データセット
uspto-grants-1983_01
特許番号
US04369184

反応ノート

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