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

반응식

HRID 437654 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e5def43fac7e4e6cad4bef77afdbb986
출처 데이터셋
uspto-grants-1977_06
특허 번호
US04031226

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