Chloroform → 1-Methyl-3-cyclooctylmethylaminocarbonylpiperidine

HRID 1609499Notes

Reaction equation

HRID 1609499 reaction equation
C(Cl)(Cl)Cl.Cl.[CH3:6][N:7]1[CH2:15][CH2:14][CH2:13][CH:9]([C:10]([OH:12])=O)[CH2:8]1.ClC(OCC(C)C)=O.[CH:24]1([CH2:32][NH2:33])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>C(N(CC)CC)C>[CH3:6][N:7]1[CH2:15][CH2:14][CH2:13][CH:9]([C:10]([NH:33][CH2:32][CH:24]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[O:12])[CH2:8]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 62365Isobutyl chloroformateHCID 78473CyclooctylmethylamineHCID 125147111-Methylpiperidine-3-carboxylic acid hydrochloride

Product 1

HCID 200816741-Methyl-3-cyclooctylmethylaminocarbonylpiperidineYield 62%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 80 ml of chloroform were added 3.59 g of 1-methylnipecotic acid hydrochloride and 6.26 ml of triethylamine. Thereto was added 3.0 g of isobutyl chloroformate under ice cooling and stirring. The mixture was stirred for 30 minutes. Thereto was added 3.1 g of cyclooctylmethylamine, and the mixture was subjected to a reaction for 2 hours at room temperature. The reaction mixture was washed with an aqueous sodium hydrogen carbonate solution and with water, and dried with anhydrous sodium sulfate. The solvent was removed by evaporation. The residue was purified by a Silica gel column chromatography (dichloromethane:methanol=10:1) to obtain 3.3 g of 1-methyl-3-cyclooctylmethylaminocarbonylpiperidine.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. customthe mixture was subjected to a reaction for 2 hours at room temperature
  3. washThe reaction mixture was washed with an aqueous sodium hydrogen carbonate solution and with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was removed by evaporation
  6. customThe residue was purified by a Silica gel column chromatography (dichloromethane:methanol=10:1)

Sources & evidence

ORD record
ord-d2ac01b34b084871b2b36b8b9837e8d9
Source dataset
uspto-grants-1995_03
Patent number
US05401740

Reaction notes

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