2-Bromopropane → HCID 23541247, compound

HRID 1867689Notes

Reaction equation

HRID 1867689 reaction equation
[CH3:1][NH:2][C:3]1([C:9]([NH2:11])=[O:10])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].Br[CH:19]([CH3:21])[CH3:20]>C(#N)C>[CH:19]([N:6]1[CH2:7][CH2:8][C:3]([NH:2][CH3:1])([C:9]([NH2:11])=[O:10])[CH2:4][CH2:5]1)([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 964744-(Methylamino)piperidine-4-carboxamide

Product 1

HCID 23541247HCID 23541247, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(methylamino)piperidine-4-carboxamide (250 mg, 1.59 mmol), potassium carbonate (264 mg, 1.91 mmol) and 2-bromopropane (0.179 ml, 1.91 mmol) in acetonitrile (10 ml) were heated at reflux for 1.5 hours. The mixture was cooled, filtered and concentrated under reduced pressure. The residues were purified by column chromatography on silica eluting with ammonia in methanol/dichloromethane (90/10) to give 1-isopropyl-4-(methylamino)piperidine-4-carboxamide (153 mg, 48%) as a white solid. 1H NMR Spectrum: (DMSO-d6) 0.92 (d, 6H); 1.45 (m, 2H); 1.77 (m, 2H); 1.86 (s, 1H); 2.06 (s, 3H); 2.38 (m, 4H); 2.59 (m, 1H); 6.82 (s, 1H); 7.15 (s, 1H).

Workup

  1. temperatureat reflux for 1.5 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residues were purified by column chromatography on silica eluting with ammonia in methanol/dichloromethane (90/10)

Sources & evidence

ORD record
ord-c6cfeaa335ab4f7ca3e4186938244ed8
Source dataset
uspto-grants-2009_12
Patent number
US07632840B2

Reaction notes

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