Piperidine-1-carboximidamide Hydrochloride → HCID 67517523, compound

HRID 2278444Notes

Reaction equation

HRID 2278444 reaction equation
CN(C)[CH:3]=[C:4]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=1)[C:5]([C:7]1[CH:11]=[CH:10][O:9][C:8]=1[CH3:12])=O.[ClH:21].[N:22]1([C:28](=[NH:30])[NH2:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.CC(C)([O-])C.[K+]>C(O)C>[ClH:21].[CH3:12][C:8]1[O:9][CH:10]=[CH:11][C:7]=1[C:5]1[C:4]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=2)=[CH:3][N:29]=[C:28]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[N:30]=1

Participants

5

Reactant 3

HCID 11217425Piperidine-1-carboximidamide HydrochlorideHCID 23665647Potassium tert-butoxideHCID 67513546HCID 67513546, compound

Product 1

HCID 67517523HCID 67517523, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-(dimethylamino)-1-(2-methyl-3-f uranyl)-2-(2-methyl-4-pyridinyl)-2-propen-1-one (270 mg, 1 mmol) and 1-piperidinecarboximidamide hydrochloride (245 mg, 1.500 mmol) in ethanol (4 ml) was stirred at room temperature. Potassium tert-butoxide (224 mg, 2.000 mmol) was added and the mixture was heated at reflux for 90 minutes. After cooling to room temperature the solvent was evaporated and the residue was diluted with water and extracted with ethyl acetate. The organic extracts were combined, washed with water and brine, dried and evaporated. The residue was purified by silica gel chromatography eluting with 30-100% ethyl acetate in isohexane. The resulting oil was dissolved in dichloromethane (2 ml) and was treated with hydrogen chloride (1M in diethyl ether, 1 ml). The solvent was evaporated and the residue co-evaporated with diethyl ether (×2). The residue was triturated with diethyl ether and the resulting solid was collected, washed with diethyl ether and dried to give the title compound as a pale yellow solid (114 mg, 31%). LC/MS [M+H]+=335. 1H NMR (400 MHz, d6-DMSO): δ 8.60 (2H, d), 8.55 (1H, s), 7.83 (1H, b), 7.58-7.54 (1H, m), 7.51 (1H, d), 6.03 (1H, d), 3.90-3.85 (4H, m), 2.67 (3H, s), 2.38 (3H, s), 1.70-1.53 (6H, m).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 90 minutes
  3. temperatureAfter cooling to room temperature the solvent
  4. customwas evaporated
  5. additionthe residue was diluted with water
  6. extractionextracted with ethyl acetate
  7. washwashed with water and brine
  8. customdried
  9. customevaporated
  10. customThe residue was purified by silica gel chromatography
  11. washeluting with 30-100% ethyl acetate in isohexane
  12. dissolutionThe resulting oil was dissolved in dichloromethane (2 ml)
  13. additionwas treated with hydrogen chloride (1M in diethyl ether, 1 ml)
  14. customThe solvent was evaporated
  15. customThe residue was triturated with diethyl ether
  16. customthe resulting solid was collected
  17. washwashed with diethyl ether
  18. customdried

Sources & evidence

ORD record
ord-d7e16833e16d4b27b1d46e849be63ed3
Source dataset
uspto-grants-2015_09
Patent number
US09133178B2

Reaction notes

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