Ammonium formate → 4-(2-Ethyl-4,5,6,7-tetrahydro-2h-indazol-3-yl)piperidine

HRID 1357939Notes

Reaction equation

HRID 1357939 reaction equation
[CH2:1]([N:3]1[C:11]([CH:12]2[CH2:17][CH2:16][N:15](CC3C=CC=CC=3)[CH2:14][CH2:13]2)=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)=[N:4]1)[CH3:2].C([O-])=O.[NH4+]>CO.[OH-].[OH-].[Pd+2]>[CH2:1]([N:3]1[C:11]([CH:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)=[N:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 219127834-(2-Ethyl-4,5,6,7-tetrahydro-(2H)-indazol-3-yl)-1-benzylpiperidine

Product 1

HCID 219127464-(2-Ethyl-4,5,6,7-tetrahydro-2h-indazol-3-yl)piperidineYield 97.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 0.273 g 4-(2-ethyl-4,5,6,7-tetrahydro-(2H)-indazol-3-yl)-1-benzylpiperidine from Step B above, 0.789 g ammonium formate, and 35 mg 20% Pd(OH)2 in 6 mL methanol was heated at 65° C. for 1 h. Basic aqueous work-up with ether extraction provided 0.192 g title compound as a colorless solid (97%).

Workup

  1. extractionBasic aqueous work-up with ether extraction

Sources & evidence

ORD record
ord-ad5c60d37e4f4ebea26977d27ca317f0
Source dataset
uspto-grants-2003_07
Patent number
US06593346B2

Reaction notes

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