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

HRID 981629Notes

Reaction equation

HRID 981629 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d707f80d7d5e4845a9a72f38cdfc00a9
Source dataset
uspto-grants-1991_02
Patent number
US04992433

Reaction notes

Loading…