Methylhydrazine → HCID 69447489, compound

HRID 1593010Notes

Reaction equation

HRID 1593010 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=O)[CH2:15][C:16](=O)[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][NH:27][NH2:28]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:27]([CH3:26])[N:28]=[C:16]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 18187492Tert-butyl 4-(3-oxo-4-phenylbutanoyl)piperidine-1-carboxylate

Product 1

HCID 69447489HCID 69447489, compoundYield 26.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

4-(3-Oxo-4-phenyl-butyryl)-piperidine-1-carboxylic acid tert-butyl ester (0.118 g) was dissolved in MeOH (4 mL) and added to a refluxing solution of methyl hydrazine (0.019 g) in methanol (2 mL). After 45 minutes at reflux the reaction mixture was cooled to room temperature and solvents evaporated under reduced pressure to give the crude product as a clear oil which was purified by column chromatography on silica using Et2O as eluent to give 4-(5-benzyl-2-methyl-2H-pyrazol-3-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.032 g) as a clear oil; NMR (CDCl3): 1.46 (s, 9H), 1.46-1.54 (m, 2H), 1.82 (br d, 2H), 2.64 (tt, 1H), 2.78 (br t, 2H), 3.77 (s, 3H), 3.90 (s, 2H), 4.18 (br d, 2H), 5.72 (s, 1H), 7.16-7.29 (m, 5H); MS: 356 (MH+).

Workup

  1. temperatureAfter 45 minutes at reflux the reaction mixture
  2. customsolvents evaporated under reduced pressure
  3. customto give the crude product as a clear oil which
  4. customwas purified by column chromatography on silica

Sources & evidence

ORD record
ord-7c1a6497bf8d4425a5780a0df8b15ff5
Source dataset
uspto-grants-2007_11
Patent number
US07294636B2

Reaction notes

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