Potassium Carbonate → HCID 21220988, compound

HRID 1584876Notes

Reaction equation

HRID 1584876 reaction equation
C1(C)C=CC(S(O[CH2:11][CH:12]2[O:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[O:14][CH2:13]2)(=O)=O)=CC=1.FC(F)(F)C(O)=O.[NH2:30][C:31]1[C:36]([C:37]([NH:39][CH2:40][CH:41]2[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]2)=[O:38])=[CH:35][CH:34]=[CH:33][N:32]=1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)/C=C\C(O)=O>C(#N)C>[NH2:30][C:31]1[C:36]([C:37]([NH:39][CH2:40][CH:41]2[CH2:46][CH2:45][N:44]([CH2:11][CH:12]3[O:17][C:16]4[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=4[O:14][CH2:13]3)[CH2:43][CH2:42]2)=[O:38])=[CH:35][CH:34]=[CH:33][N:32]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 444266Maleic AcidHCID 4522296(2,3-Dihydrobenzo[b][1,4]dioxin-2-yl)methyl 4-methylbenzenesulfonateHCID 21221049HCID 21221049, compound

Product 1

HCID 21220988HCID 21220988, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 1,4-benzodioxan-2-ylmethyl toluene4-sulphonate (0.82 g), 2-amino-N-(4-piperidylmethyl)pyridine-3-carboxamide trifluoroacetate (0.905 g; prepared in a similar manner to that described in Example 2) and potassium carbonate (1.4 g) in acetonitrile (50 ml) was heated under reflux for 6 hours. After cooling, the solvent was removed in vacuo, water (60 ml) was added to the residue, and the product was extracted with dichloromethane (2×30 ml). The extracts were dried over magnesium sulphate and the solvent was removed in vacuo to give an oil. The oil was purified by flash chromatography on silica eluting with a 9:1 then 1:1 mixture of dichloromethane and methanol. Appropriate fractions were combined and the solvents removed in vacuo to give an oil. Ethereal maleic acid (20 ml) was added to yield a white solid. The solid was collected by filtration, washed with ether and the solvent removed in vacuo to yield 2-amino-N-{[1-(1,4-benzodioxan-2-ylmethyl)-4-piperidyl]methyl}pyridine-3-carboxamide 0.5 maleate (95 mg) m.p. 104-106° C.

Workup

  1. customprepared in a similar manner to that
  2. temperaturewas heated
  3. temperatureunder reflux for 6 hours
  4. temperatureAfter cooling
  5. customthe solvent was removed in vacuo, water (60 ml)
  6. additionwas added to the residue
  7. extractionthe product was extracted with dichloromethane (2×30 ml)
  8. dry with materialThe extracts were dried over magnesium sulphate
  9. customthe solvent was removed in vacuo
  10. customto give an oil
  11. customThe oil was purified by flash chromatography on silica eluting with a 9:1
  12. addition1:1 mixture of dichloromethane and methanol
  13. customthe solvents removed in vacuo
  14. customto give an oil
  15. customto yield a white solid
  16. filtrationThe solid was collected by filtration
  17. washwashed with ether
  18. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-6bf77b7540d24739bdf4959175d42839
Source dataset
uspto-grants-1999_08
Patent number
US05935973

Reaction notes

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