Potassium Hydroxide → HCID 15718981, compound

HRID 2166151Notes

Reaction equation

HRID 2166151 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]3[N:23]([CH2:24][CH2:25][NH:26]C(=O)OCC)[C:18]4=[N:19][CH:20]=[CH:21][CH:22]=[C:17]4[N:16]=3)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>CC(O)C>[C:1]1([CH2:7][N:8]2[CH2:9][CH2:10][CH:11]([NH:14][C:15]3[N:23]([CH2:24][CH2:25][NH2:26])[C:18]4=[N:19][CH:20]=[CH:21][CH:22]=[C:17]4[N:16]=3)[CH2:12][CH2:13]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15718991HCID 15718991, compound

Product 1

HCID 15718981HCID 15718981, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 20 parts of ethyl [2-[2-[[1-(phenylmethyl)-4-piperidinyl]amino]-3H-imidazo[4,5-b]-pyridin-3-yl]ethyl]carbamate, 26.3 parts of potassium hydroxide and 200 parts of 2-propanol was stirred for 1.5 hour at reflux temperature. The reaction mixture was evaporated and the residue was taken up in water. The whole was evaporated again. The residue was taken up in a small amount of water and 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, saturated with ammonia, (90:10 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was boiled in 2,2'-oxybispropane (+activated charcoal) and the whole was filtered over diatomaceous earth. The filtrate was allowed to crystallize. The crystallized product was filtered off (the filtrate was set aside) and dried, yielding a first fraction of 6.7 parts (40.6%) of 2-[[1-(phenylmethyl)-4-piperidinyl]amino]-3H-imidazo[4,5-b]pyridine-3-ethanamine. The filtrate, which was set aside (see above) was evaporated, yielding a second fraction of 6.6 parts (40.0%) of 2-[[1-(phenylmethyl)-4-piperidinyl]amino]-3H-imidazo[4,5-b]pyridine-3-ethanamine. Total yield: 13.3 parts (80.6%) of 2-[[1-(phenylmethyl)-4-piperidinyl]amino]-3H-imidazo[4,5-b]pyridine-3-ethanamine; mp. 101.7° C. (compound 187).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. customThe whole was evaporated again
  4. extractionthe product was extracted with dichloromethane
  5. customThe extract was dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. filtrationwas filtered over diatomaceous earth
  13. customto crystallize
  14. filtrationThe crystallized product was filtered off (the filtrate
  15. customdried

Sources & evidence

ORD record
ord-eee1243faee7499fa5ebc1e60845a4ea
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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