Ethanol → 7,7-dimethyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine dihydrochloride

HRID 74524Notes

Reaction equation

HRID 74524 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C:9]1([CH3:25])[CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][C:11]2[CH:22]=[N:23][NH:24][C:10]1=2.C(O)C.[Cl:29]CCl>>[ClH:29].[ClH:29].[CH3:8][C:9]1([CH3:25])[CH2:14][NH:13][CH2:12][C:11]2[CH:22]=[N:23][NH:24][C:10]1=2

Participants

5

Reactant 4

HCID 702EthanolHCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 37818370tert-Butyl 7,7-dimethyl-1,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxylate

Product 1

HCID 667221937,7-dimethyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine dihydrochloride

Procedure

At 0° C. 5 mL trifluoroacetic acid was added to 1.60 g (6.05 mmol) tert-butyl 7,7-dimethyl-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylate (synthesised analogously to WO2005/065779) in 15 mL dichloromethane and the reaction mixture was stirred for 2 h at RT. Then the solvent was eliminated i. vac. The residue was combined with ethanol and evaporated down again i. vac. The residue was dissolved in ethanol and 12 mL of a 1.25 M ethanolic HCl solution were added. The mixture was again evaporated down i. vac. The residue was triturated with ethanol. The solid was suction filtered and dried.

Workup

  1. customAt 0° C
  2. customevaporated down again i
  3. dissolutionThe residue was dissolved in ethanol
  4. addition12 mL of a 1.25 M ethanolic HCl solution were added
  5. customThe mixture was again evaporated down i
  6. customThe residue was triturated with ethanol
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-8c41f994a3a248d298e38112a51ac50f
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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