1-Piperazinecarboxylic acid, ethyl ester → HCID 19911567, compound

HRID 1708916Notes

Reaction equation

HRID 1708916 reaction equation
[N:1]1([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl[CH2:13][C:14]1[N:22]([CH2:23][CH2:24][OH:25])[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:16]2[N:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[OH:25][CH2:24][CH2:23][N:22]1[C:17]2=[N:18][CH:19]=[CH:20][CH:21]=[C:16]2[N:15]=[C:14]1[CH2:13][N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 10340Sodium CarbonateHCID 19911553HCID 19911553, compound

Product 1

HCID 19911567HCID 19911567, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 13.5 parts of ethyl 1-piperazinecarboxylate and 160 parts of ethanol were added 18 parts of 2-(chloromethyl)-3H-imidazo[4,5-b]pyridine-3-ethanol. After the addition of 10.6 parts of sodium carbonate, the reaction mixture was stirred for 32 hours at reflux temperature. The whole was evaporated and the residue taken up in water. The product was extracted with dichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of dichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 17.5 parts (62.7%) of ethyl 4-[[3-(2-hydroxyethyl)-3H-imidazo-[4,5-b]pyridin-2-yl]methyl]-1-piperazinecarboxylate; mp. 117.4° C. (compound 18).

Workup

  1. temperatureat reflux temperature
  2. customThe whole was evaporated
  3. extractionThe product was extracted with dichloromethane
  4. washThe extract was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of dichloromethane and methanol (95:5 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. customThe residue was crystallized from 2,2'-oxybispropane
  13. filtrationThe product was filtered off
  14. customdried

Sources & evidence

ORD record
ord-a4e7e7e0f63b470e96baf7cb881b25e2
Source dataset
uspto-grants-1990_08
Patent number
US04946843

Reaction notes

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