Triethylamine → HCID 47215822, compound

HRID 1398080Notes

Reaction equation

HRID 1398080 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:22][N:23]([CH3:28])[S:24](Cl)(=[O:26])=[O:25].C(OCC)(=O)C>ClCCl>[CH3:22][N:23]([CH3:28])[S:24]([N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8]([O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:14])[CH2:5][CH2:6]1)(=[O:26])=[O:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 83372Dimethylsulphamoyl chlorideHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 47215822HCID 47215822, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 412 mg (2.06 mmol) of tert-butyl 4-piperidinylcarbamate in 20 mL of dichloromethane were added 430 μL (3.09 mmol) of triethylamine and 265 μL (2.47 mmol) of dimethylsulfamoyl chloride and the mixture was stirred for 2 hours at room temperature. Then, the mixture was treated with ethyl acetate and the organic layer was washed with water and saturated saline solution, and then, dried over with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=40/1) to give 536 mg (85%) of the title compound.

Workup

  1. washthe organic layer was washed with water and saturated saline solution
  2. dry with materialdried over with anhydrous sodium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=40/1)

Sources & evidence

ORD record
ord-0cf33017e07842c8b3d70d98eebe9c44
Source dataset
uspto-grants-2014_12
Patent number
US08901315B2

Reaction notes

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