Methylhydrazine → HCID 18436984, compound

HRID 2111743Notes

Reaction equation

HRID 2111743 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:17]=2F)=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][NH:28][NH2:29].C([O-])(O)=O.[Na+]>C(O)CCC>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[C:16]3[C:17](=[CH:18][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=3)[N:28]([CH3:27])[N:29]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6061MethylhydrazineHCID 516892Sodium BicarbonateHCID 23112486HCID 23112486, compound

Product 1

HCID 18436984HCID 18436984, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of (1-benzyl-piperidin-4-yl)-(2-fluoro-4-trifluoromethyl-phenyl)-methanone (2.0 g, 5.46 mmol), methylhydrazine (327 mg, 7.10 mmol), and n-butanol (22 mL) was heated at 120° C. in a seal vessel for 18 hours. The reaction was cooled to room temperature and basified with NaHCO3 and extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine (50 mL), dried over magnesium sulfate, filtered, and evaporated. The product was chromatographed on silica, eluting with 1:1 ethyl acetate/heptane, to afford 1.68 g (82%) of the desired product as an oil.

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined organic layers were washed with brine (50 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe product was chromatographed on silica
  7. washeluting with 1:1 ethyl acetate/heptane

Sources & evidence

ORD record
ord-ae64edffce324895a1ccdfc63cd87dd1
Source dataset
uspto-grants-2009_04
Patent number
US07521445B2

Reaction notes

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