Ammonium Chloride → 2-(2-piperidin-1-yl-ethyl)-2H-indazol-5-ylamine

HRID 1825830Notes

Reaction equation

HRID 1825830 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:10]2[C:6](=[CH:7][N:8]([CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[N:9]=2)[CH:5]=1)([O-])=O.[Cl-].[NH4+].[CH2:22](O)C.O>[Fe]>[N:15]1([CH2:14][CH2:13][N:8]2[CH:7]=[C:6]3[C:10]([CH:11]=[CH:12][C:4]([NH2:1])=[CH:5]3)=[N:9]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:22]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 19096565Water ethanolHCID 221389045-Nitro-2-(2-(pyrrolidin-1-yl)ethyl)-2H-indazole

Product 1

HCID 221389012-(2-piperidin-1-yl-ethyl)-2H-indazol-5-ylamine

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

5-Nitro-2-(2-pyrrolidin-1-yl-ethyl)-2H-indazole (0.325 g, 1.18 mmol), iron powder (0.659 g, 11.8 mmol) and ammonium chloride (0.0317 g, 0.592 mmol) was suspended in a 4:1 ethanol/H2O solution and heated to reflux for 3 hours. The mixture was cooled to room temperature, the solvent were removed in vacuo and the residue stirred in triethylamine/ethyl acetate (1/4, 30 mL) for 15 minutes. The mixture was filtered through a plug of silica gel, rinsed with triethylamine/ethyl acetate (1/4) and the filtrate was concentrated to afford the title product. 1H NMR (300 MHz, DMSO-d6) ppm 1.31–1.52 (m, 6H) 2.40 (m, 4H), 2.78 (m, 2H), 4.38 (t, 2H, J=6.78), 4.79 (s, 2H), 6.55 (m, 1H), 6.72 (m, 1H), 7.29 (s, 1H), 7.89 (s, 1H); MS (DCI/NH3) m/z 245 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 hours
  3. customthe solvent were removed in vacuo
  4. filtrationThe mixture was filtered through a plug of silica gel
  5. washrinsed with triethylamine/ethyl acetate (1/4)
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f41cd6a2c5ec4f61b0841f091e62bbc3
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Reaction notes

Loading…