Acetic Anhydride → 1-(3-((4-nitro-1H-indazol-1-yl)methyl)piperidin-1-yl)ethanone

HRID 706714Notes

Reaction equation

HRID 706714 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][N:8]2[CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]1)([O-:3])=[O:2].C(N(CC)CC)C.[C:27](OC(=O)C)(=[O:29])[CH3:28]>C(Cl)Cl>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][N:8]2[CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][N:16]([C:27](=[O:29])[CH3:28])[CH2:15]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 679761024-nitro-1-(piperidin-3-ylmethyl)-1H-indazole

Product 1

HCID 679745911-(3-((4-nitro-1H-indazol-1-yl)methyl)piperidin-1-yl)ethanoneYield 52.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-nitro-1-(piperidin-3-ylmethyl)-1H-indazole (0.050 g, 0.139 mmol), triethylamine (0.097 mL, 0.699 mmol) in DCM (1 mL) was treated with acetic anhydride (0.0158 mL, 0.168 mmol) at ambient temperature and stirring continued for 1 hour. The mixture was quenched with saturated aqueous sodium bicarbonate, extracted with DCM, dried (phase separator silicone treated filter paper) and concentrated to provide 1-(3-((4-nitro-1H-indazol-1-yl)methyl)piperidin-1-yl)ethanone (0.022 g, 52% yield) as a yellow oil.

Workup

  1. customThe mixture was quenched with saturated aqueous sodium bicarbonate
  2. extractionextracted with DCM
  3. customdried
  4. addition(phase separator silicone treated filter paper)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4401c4df7ecc4bcdb731aef308c135d0
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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