Triethylamine → Methyl 2-(1-methyl-3-(N-(4-octylphenyl)sulfamoylamino)piperidin-3-yl)acetate

HRID 1192900Notes

Reaction equation

HRID 1192900 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16](NC(=O)OCCCl)(=[O:18])=[O:17])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:26]CN(CC)CC.[NH2:33][C:34]1([CH2:41][C:42]([O-:44])=[O:43])[CH2:39][CH2:38][CH2:37][N:36]([CH3:40])[CH2:35]1>CC#N>[CH3:40][N:36]1[CH2:37][CH2:38][CH2:39][C:34]([CH2:41][C:42]([O:44][CH3:26])=[O:43])([NH:33][S:16](=[O:17])(=[O:18])[NH:15][C:12]2[CH:11]=[CH:10][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:14][CH:13]=2)[CH2:35]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 581099762-chloroethyl N-(4-octylphenyl)sulfamoylcarbamateHCID 866498462-(3-Amino-1-methylpiperidin-3-yl)acetate

Product 1

HCID 66864494Methyl 2-(1-methyl-3-(N-(4-octylphenyl)sulfamoylamino)piperidin-3-yl)acetateYield 27.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-chloroethyl N-(4-octylphenyl)sulfamoylcarbamate (156 mg, 0.4 mmol) in CH3CN (10 mL) was treated with Et3N (0.14 mL, 1 mmol) and refluxed for 25 min. and cooled. A solution of 2-(3-amino-1-methylpiperidin-3-yl)acetate (62 mg, 0.33 mmol) was added and the resulting mixture was refluxed for 4 h. After removal of the solvent in vacuo, the residue was dissolved in dichloromethane (40 mL) and washed with sat. NaHCO3 (10 mL), H2O (10 mL), brine (10 mL) and dried (Na2SO4). After evaporation, the residue was purified by flash chromatography (EtOAc/hex 1:4 to EtOAc) to give the title compound (41 mg, 27%) as colorless oil. MS ESI 454.3[M+H]+, calcd for [C23H39N3O4S+H]+ 454.27.

Workup

  1. temperaturerefluxed for 25 min.
  2. temperaturecooled
  3. temperaturethe resulting mixture was refluxed for 4 h
  4. customAfter removal of the solvent in vacuo
  5. dissolutionthe residue was dissolved in dichloromethane (40 mL)
  6. washwashed with sat. NaHCO3 (10 mL), H2O (10 mL), brine (10 mL)
  7. dry with materialdried (Na2SO4)
  8. customAfter evaporation
  9. customthe residue was purified by flash chromatography (EtOAc/hex 1:4 to EtOAc)

Sources & evidence

ORD record
ord-fd1b85da27084615b130ce0d77af19db
Source dataset
uspto-grants-2014_03
Patent number
US08680282B2

Reaction notes

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