Potassium Hydroxide → N-[4-(4,5-dihydro-2-oxazolyl)phenyl]-4-piperidinemethanamine

HRID 981629노트

반응식

HRID 981629 반응식
[O:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17](C(OCC)=O)[CH2:16][CH2:15]2)=[CH:8][CH:7]=1.[OH-].[K+]>CC(O)C>[O:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]([NH:12][CH2:13][CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:10][CH:11]=1

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 14989211Ethyl 4-[[[4-(4,5-dihydro-2-oxazolyl)phenyl]amino]methyl]-1-piperidinecarboxylate

생성물 1

HCID 19748280N-[4-(4,5-dihydro-2-oxazolyl)phenyl]-4-piperidinemethanamine수율 49.1%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A mixture of 13.3 parts of ethyl 4-[[[4-(4,5-dihydro-2-oxazolyl)phenyl]amino]-methyl]-1-piperidinecarboxylate, 22.4 parts of potassium hydroxide and 240 parts of 2-propanol was stirred for 6 hours at reflux temperature. The reaction mixture was evaporated. The residue was taken up in water and the whole was evaporated again till all traces of 2-propanol were removed. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 5.1 parts (49.1%) of N-[4-(4,5-dihydro-2-oxazolyl)phenyl]-4-piperidinemethanamine as a residue (int. 77).

후처리

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. customthe whole was evaporated again till all traces of 2-propanol
  4. customwere removed
  5. extractionThe product was extracted with dichloromethane
  6. customThe extract was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by column chromatography over silica gel using
  10. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  11. customThe pure fractions were collected
  12. customthe eluent was evaporated

출처 및 근거

ORD 기록
ord-d707f80d7d5e4845a9a72f38cdfc00a9
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04992433

반응 노트

불러오는 중…