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

HRID 1192916Notes

Reaction equation

HRID 1192916 reaction equation
N[C:2]1([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:7][CH2:6][CH2:5][N:4]([CH3:8])[CH2:3]1.CCN(CC)CC.Cl[S:22]([NH:25][C:26](=O)OCCCl)(=[O:24])=[O:23].C[NH:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:36][CH:35]=1>C(Cl)Cl.CC#N>[CH3:8][N:4]1[CH2:5][CH2:6][CH2:7][C:2]([CH2:9][C:10]([O:12][CH3:13])=[O:11])([N:25]([CH3:26])[S:22](=[O:23])(=[O:24])[NH:33][C:34]2[CH:39]=[CH:38][C:37]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:36][CH:35]=2)[CH2:3]1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 131188122-Chloroethyl chlorosulfonylcarbamateHCID 17827013N-methyl-4-octylanilineHCID 66864584Methyl 2-(3-amino-1-methylpiperidin-3-yl)acetate

Product 1

HCID 66864939Methyl 2-(1-methyl-3-(N-methyl-N-(4-octylphenyl)sulfamoylamino)piperidin-3-yl)acetateYield 22%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 2-(3-amino-1-methylpiperidin-3-yl)acetate (186 mg, 1 mmol) and Et3N (0.42 mL, 3 mmol) in CH2Cl2 was added the solution of 2-chloroethyl chlorosulfonylcarbamate in CH2Cl2 (0.77 M, 1.3 mL, 1 mmol). After addition, the resulting mixture was stirred overnight at rt. Evaporation of solvents gave a light yellow oil which was used without further purification. A solution of this crude mixture, N-methyl-4-octylaniline (241 mg, 1.1 mmol) and Et3N (0.42 mL, 3 mmol) in CH3CN (10 mL) was refluxed for 2 h. After cooling to rt and evaporating solvents, the residue was purified by a short column (EtOAc/hexance=10:1) to give the title compound (105 mg, 22%) as white solid. MS ESI 468.3 [M+H]+, calcd for [C24H41N3O4S+H]+ 468.29.

Workup

  1. additionAfter addition
  2. customEvaporation of solvents
  3. customgave a light yellow oil which
  4. customwas used without further purification
  5. temperatureAfter cooling to rt
  6. customevaporating solvents
  7. customthe residue was purified by a short column (EtOAc/hexance=10:1)

Sources & evidence

ORD record
ord-db0448d255ff46a59408ab78dcf93b73
Source dataset
uspto-grants-2014_03
Patent number
US08680282B2

Reaction notes

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