O-Phenylenediamine → 2-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-benzimidazole

HRID 1904819노트

반응식

HRID 1904819 반응식
Cl.[C:2]1([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][C:16](O)=O)[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]1([NH2:26])[C:20]([NH2:25])=[CH:21][CH:22]=[CH:23][CH:24]=1.[OH-].[K+]>O>[C:2]1([CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][C:16]3[NH:26][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[N:25]=3)[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 7243O-PhenylenediamineHCID 14797Potassium HydroxideHCID 140128442-(1-Benzylpiperidin-4-yl)acetic acid hydrochloride

생성물 1

HCID 140128452-[[1-(phenylmethyl)-4-piperidinyl]methyl]-1H-benzimidazole

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To 73 parts of hot (70° C.) polyphosphoric acid were added 27 parts of 1-(phenylmethyl)-4-piperidineacetic acid hydrochloride: temperature rose to 100° C. When the addition was complete, there were added portionwise 14 parts of 1,2-benzenediamine and stirring and heating was continued for 50 minutes at 170° C. The hot reaction mixture was poured into 300 parts of warm water. The acid solution was alkalized with a potassium hydroxide solution. The precipitated free base was filtered off, washed with water and extracted with trichloromethane. The extract was dried and evaporated. The solid residue was recrystallized from a mixture of 2-propanone and methanol, yielding 17 parts of 2-[[1-(phenylmethyl)-4-piperidinyl]-methyl]-1H-benzimidazole; mp. 221.5°-222° C. (compound 1).

후처리

  1. customrose to 100° C
  2. additionWhen the addition
  3. temperatureheating
  4. filtrationThe precipitated free base was filtered off
  5. washwashed with water
  6. extractionextracted with trichloromethane
  7. customThe extract was dried
  8. customevaporated
  9. customThe solid residue was recrystallized from a mixture of 2-propanone and methanol

출처 및 근거

ORD 기록
ord-cd7c051a93894835a3416bb5c78bcfc8
출처 데이터셋
uspto-grants-1989_06
특허 번호
US04839374

반응 노트

불러오는 중…