Potassium Hydroxide → HCID 15718815, compound

HRID 2166130Notes

Reaction equation

HRID 2166130 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[N:6]=[C:5]1[NH:13][CH:14]1[CH2:19][CH2:18][N:17](C(OCC)=O)[CH2:16][CH2:15]1.[OH-].[K+]>CC(O)C>[NH:17]1[CH2:16][CH2:15][CH:14]([NH:13][C:5]2[N:4]([CH2:3][CH2:2][OH:1])[C:8]3=[N:9][CH:10]=[CH:11][CH:12]=[C:7]3[N:6]=2)[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15718794HCID 15718794, compound

Product 1

HCID 15718815HCID 15718815, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 14 parts of ethyl 4-[[3-(2-hydroxyethyl)-3H-imidazo[4,5-b]pyridin-2-yl]amino]-1-piperidinecarboxylate, 22 parts of potassium hydroxide and 160 parts of 2-propanol was stirred overnight at reflux temperature. The reaction mixture was evaporated and the residue was taken up in water. The aqueous layer was salted out with potassium carbonate and the product was extracted with tetrahydrofuran. The extract was dried, filtered and evaporated. The residue was crystallized from acetonitrile. The product was filtered off and dried, yielding 5.5 parts (52.3%) of 2-(4-piperidinylamino)-3H-imidazo[4,5-b]pyridine-3-ethanol; mp. 156.9° C. (compound 20).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. extractionthe product was extracted with tetrahydrofuran
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was crystallized from acetonitrile
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-b6a622b2c9a544319e3a8576ffe67bea
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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