Ethanol → HCID 89709226, compound

HRID 1526198Notes

Reaction equation

HRID 1526198 reaction equation
[CH:1]1([N:4]2[CH2:9][CH2:8][CH:7]([N:10]3[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[N:11]3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.C(O)C.O.[Cl-].[NH4+]>[Fe].CO.C(Cl)(Cl)Cl>[CH:1]1([N:4]2[CH2:9][CH2:8][CH:7]([N:10]3[CH:14]=[C:13]([NH2:15])[CH:12]=[N:11]3)[CH2:6][CH2:5]2)[CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 117667469HCID 117667469, compound

Product 1

HCID 89709226HCID 89709226, compoundYield 67.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-cyclopropyl-4-(4-nitro-1H-pyrazol-1-yl)piperidine (952 mg), ethanol (6 mL), water (2 mL), and ammonium chloride (108 mg) was heated to 80° C., and iron powder (1.13 g) was added thereto, followed by stirring at 80° C. for 3 hours. Chloroform and methanol were added thereto, followed by filtration through celite, and the organic phase was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=1:0:0-95:4.5:0.5, NH2 type: eluent; hexane:ethyl acetate=3:7-0:1) to obtain 1-(1-cyclopropylpiperidin-4-yl)-1H-pyrazol-4-amine (558 mg) as a pale pink solid.

Workup

  1. filtrationfollowed by filtration through celite
  2. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (eluent; chloroform:methanol:28% aqueous ammonia=1:0:0-95:4.5:0.5, NH2 type: eluent; hexane:ethyl acetate=3:7-0:1)

Sources & evidence

ORD record
ord-37b1c6b76fc049a3b55e9f1be28c0ff8
Source dataset
uspto-grants-2015_07
Patent number
US09085540B2

Reaction notes

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