Benzene → N-[2-{4-[3-(2-cyanoethyl)-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl]-1-piperidinyl}ethyl]-4-fluorobenzamide

HRID 437667

반응식

HRID 437667 반응식
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]2[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.Cl.[O:14]=[C:15]1[N:19]([CH2:20][CH2:21][C:22]#[N:23])[C:18]2[CH:24]=[CH:25][CH:26]=[CH:27][C:17]=2[N:16]1[CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(N(CC)CC)C.C1C=CC=CC=1>CO>[C:22]([CH2:21][CH2:20][N:19]1[C:18]2[CH:24]=[CH:25][CH:26]=[CH:27][C:17]=2[N:16]([CH:28]2[CH2:33][CH2:32][N:31]([CH2:9][CH2:10][NH:8][C:6](=[O:7])[C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:12][CH:11]=3)[CH2:30][CH2:29]2)[C:15]1=[O:14])#[N:23]

참가 물질

6

반응물 4

HCID 241BenzeneHCID 8471TriethylamineHCID 848531-(4-Fluorobenzoyl)aziridineHCID 214289232,3-dihydro-2-oxo-3-(4-piperidinyl)-1H-benzimidazole-1-propanenitrile hydrochloride

생성물 1

HCID 21428991N-[2-{4-[3-(2-cyanoethyl)-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl]-1-piperidinyl}ethyl]-4-fluorobenzamide

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 1.68 parts of 1-(4-fluorobenzoyl)aziridine, 3.07 parts of 2,3-dihydro-2-oxo-3-(4-piperidinyl)-1H-benzimidazole-1-propanenitrile hydrochloride, 1.65 parts of N,N-diethylethanamine, 10.8 parts of benzene and 1.6 parts of methanol is stirred and refluxed for 1.50 hours. The reaction mixture is cooled and poured onto water. The product is extracted with trichloromethane. The extract is dried, filtered and evaporated. The residue is crystallized from 2-propanol. The product is filtered off and recrystallized from 2-propanol, yielding 1part of N-[2-{4-[3-(2-cyanoethyl)-2,3-dihydro-2-oxo-1H-benzimidazol-1-yl]-1-piperidinyl}ethyl]-4-fluorobenzamide; mp. 172.2° C.

후처리

  1. temperaturerefluxed for 1.50 hours
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water
  4. extractionThe product is extracted with trichloromethane
  5. customThe extract is dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is crystallized from 2-propanol
  9. filtrationThe product is filtered off
  10. customrecrystallized from 2-propanol

출처 및 근거

ORD 기록
ord-d430f8b65d8c48dfbff9d02feace18b1
출처 데이터셋
uspto-grants-1977_06
특허 번호
US04031226

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