Dichloromethane → Ethyl 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-YL]amino]piperidine-1-carboxylate

HRID 582059

反応式

HRID 582059 の反応式
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2Cl)=[CH:4][CH:3]=1.[NH2:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]1.ClCCl>C(OCC)(=O)C.ClCCl>[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[NH:19][CH:20]2[CH2:21][CH2:22][N:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:24][CH2:25]2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6344DichloromethaneHCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 30202411-(4-Fluorobenzyl)-2-chlorobenzimidazole

生成物 1

HCID 3019916Ethyl 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-YL]amino]piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 21226138Dichloromethane ethylacetate溶媒

実験手順

Combine 1-(4-fluorobenzyl)-2-chloro-1H-benzimidazole (22.1 g, 84 mmol) and ethyl 4-aminopiperidine-1-carboxylate (27.7 g, 161 mmol) and heat to 170° C. After 4 hours, partition the reaction mixture between aqueous 2.5M sodium hydroxide solution and chloroform. Separate the layers and extract the aqueous layer twice with chloroform. Combine the organic layers, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on a short column of silica gel eluting sequentially with dichloromethane and then 15% ethyl acetate/dichloromethane. Evaporate the product containing fractions, triturate with hexane, filter, and dry to give (1-(4-fluorobenzyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine as a solid.

後処理

  1. custompartition the reaction mixture between aqueous 2.5M sodium hydroxide solution and chloroform
  2. customSeparate the layers
  3. extractionextract the aqueous layer twice with chloroform
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. customevaporate in vacuo
  7. customto give a residue
  8. customEvaporate the product
  9. additioncontaining fractions
  10. customtriturate with hexane
  11. filtrationfilter
  12. customdry

出典と根拠

ORDレコード
ord-b842b470e15c4a6696546cae5547762b
出典データセット
uspto-grants-1999_07
特許番号
US05922737

関連ノート

読み込み中…