Formaldehyde → N-methyl-O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl)hydroxylamine

HRID 1895924Notes

Reaction equation

HRID 1895924 reaction equation
C=O.[F:3][C:4]([F:23])([F:22])[C:5]1[CH:6]=[C:7]([S:11]([N:14]2[CH2:19][CH2:18][CH:17]([O:20][NH2:21])[CH2:16][CH2:15]2)(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1.[C:24](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(OCC)(=O)C>[CH3:24][NH:21][O:20][CH:17]1[CH2:16][CH2:15][N:14]([S:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([C:4]([F:3])([F:22])[F:23])[CH:6]=2)(=[O:13])=[O:12])[CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 67118429O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl)hydroxylamine

Product 1

HCID 86652730N-methyl-O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl)hydroxylamineYield 60%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Formaldehyde (166 mg, 5.55 mmol) was added to a solution of O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl) hydroxylamine (200 mg, 0.617 mmol) in 1,2-dichlorethane (5 ml) and stirred at room temperature for 3 hours. Sodium triacetoxyborohydride was added and stirred at room temperature for 12 hours. The reaction mixture was diluted with of ethyl acetate (30 ml), washed with H2O and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography (the residue was purified by preparative TLC (ethyl acetate/petroleum ether: 67/33) to give N-methyl-O-(1-(3-(trifluoromethyl)phenylsulfonyl)piperidin-4-yl)hydroxylamine (125 mg, 60%) as a white solid.

Workup

  1. stirringstirred at room temperature for 12 hours
  2. washwashed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (the residue
  7. customwas purified by preparative TLC (ethyl acetate/petroleum ether: 67/33)

Sources & evidence

ORD record
ord-4f729bacced04571841a441f23c72af3
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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