5-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one → ethyl {2-[4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]-ethyl}carbamate

HRID 437654

反応式

HRID 437654 の反応式
Br[CH2:2][CH2:3][NH:4][C:5](=[O:9])[O:6][CH2:7][CH3:8].[Cl:10][C:11]1[CH:26]=[CH:25][C:14]2[N:15]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[C:16](=[O:18])[NH:17][C:13]=2[CH:12]=1.C(=O)([O-])O.[Na+]>C(O)C>[Cl:10][C:11]1[CH:26]=[CH:25][C:14]2[N:15]([CH:19]3[CH2:20][CH2:21][N:22]([CH2:2][CH2:3][NH:4][C:5](=[O:9])[O:6][CH2:7][CH3:8])[CH2:23][CH2:24]3)[C:16](=[O:18])[NH:17][C:13]=2[CH:12]=1

参加物

5

反応物 3

HCID 1046075-Chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 286694ethyl N-(2-bromoethyl)carbamateHCID 516892Sodium Bicarbonate

生成物 1

HCID 54131181ethyl {2-[4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]-ethyl}carbamate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 12.94 parts of ethyl (2-bromoethyl)carbamate, 15.68 parts of 5-chloro-1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one, 10.08 parts of sodium hydrogen carbonate and 160 parts of ethanol is stirred and refluxed overnight. The formed precipitate is filtered off and washed with trichloromethane. The layers from the filtrate are separated. The organic phase is dried, filtered and evaporated. The residue is stirred in 2-propanone. The unreacted starting material is filtered off and the filtrate is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from ethanol 70%. The product is filtered off and dried, yielding 6.5 parts of ethyl {2-[4-(5-chloro-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)-1-piperidinyl]-ethyl}carbamate; mp. 187.7° C.

後処理

  1. temperaturerefluxed overnight
  2. filtrationThe formed precipitate is filtered off
  3. washwashed with trichloromethane
  4. customThe layers from the filtrate are separated
  5. customThe organic phase is dried
  6. filtrationfiltered
  7. customevaporated
  8. stirringThe residue is stirred in 2-propanone
  9. filtrationis filtered off
  10. customthe filtrate is purified by column-chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol (90:10 by volume) as eluent
  12. customThe pure fractions are collected
  13. customthe eluent is evaporated
  14. customThe residue is crystallized from ethanol 70%
  15. filtrationThe product is filtered off
  16. customdried

出典と根拠

ORDレコード
ord-e5def43fac7e4e6cad4bef77afdbb986
出典データセット
uspto-grants-1977_06
特許番号
US04031226

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