Ammonia → HCID 54385985, 화합물

HRID 437635노트

반응식

HRID 437635 반응식
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][NH:18][C:19](=[O:29])[C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[N+:26]([O-])=O)[CH2:12][CH2:11]3)[C:7](=[O:9])[NH:8][C:4]=2[CH:3]=1.O1CCCC1.[H][H].N>[Ni].CO>[NH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:19]([NH:18][CH2:17][CH2:16][N:13]1[CH2:12][CH2:11][CH:10]([N:6]2[C:5]3[CH:30]=[CH:31][C:2]([Cl:1])=[CH:3][C:4]=3[NH:8][C:7]2=[O:9])[CH2:15][CH2:14]1)=[O:29]

참가 물질

7

반응물 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 21428800HCID 21428800, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

HCID 54385985HCID 54385985, 화합물

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매2회

실험 절차

A mixture of 16 parts of N{2-[4-(5-chloro-2,3-dihydro-2-oxo- 1H-benzimidazol-1-yl)-1-piperidinyl] ethyl}-2-nitrobenzamide in 90 parts of tetrahydrofuran and 40 parts of methanol is hydrogenated at normal pressure and at room temperature with 3 parts of Raney-nickel catalyst. After the calculated amount of hydrogen is taken up, there is added a solution of methanol, previously saturated with gaseous ammonia. The catalyst is filtered off and the filtrate is evaporated. The residue is taken up in acidified water and the whole is washed twice with trichloromethane. The aqueous phase is separated and alkalized with a diluted sodium hydroxide solution. The product is extracted twice with trichloromethane. The combined extracts are washed three times with water, dried, filtered and evaporated. The residue is triturated in 2,2'-oxybispropane. The product is filtered off and crystallized from a mixture of ethanol and a small amount of water, yielding 2 parts of 2-amino-N-{2-[4-(5-chloro-2,3-dihydro-2-oxo- 1H-benzimidazol-1-yl)-1-piperidinyl] ethyl} benzamide; mp. 226.8° C.

후처리

  1. filtrationThe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. washthe whole is washed twice with trichloromethane
  4. customThe aqueous phase is separated
  5. extractionThe product is extracted twice with trichloromethane
  6. washThe combined extracts are washed three times with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is triturated in 2,2'-oxybispropane
  11. filtrationThe product is filtered off
  12. customcrystallized from a mixture of ethanol

출처 및 근거

ORD 기록
ord-157b360f0712493bb122c8d0084c6480
출처 데이터셋
uspto-grants-1977_06
특허 번호
US04031226

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