Triethylamine → Methyl 2-(1-methyl-3-(4-pentylphenylsulfonamido)piperidin-3-yl)acetate

HRID 1192897Notes

Reaction equation

HRID 1192897 reaction equation
[NH2:1][C:2]1([CH2:9][C:10]([O:12][CH2:13]C)=[O:11])[CH2:7][CH2:6][CH2:5][N:4]([CH3:8])[CH2:3]1.C(N(CC)CC)C.[CH2:22]([C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1)[CH2:23][CH2:24][CH2:25][CH3:26]>ClCCl>[CH3:8][N:4]1[CH2:5][CH2:6][CH2:7][C:2]([CH2:9][C:10]([O:12][CH3:13])=[O:11])([NH:1][S:33]([C:30]2[CH:31]=[CH:32][C:27]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:28][CH:29]=2)(=[O:35])=[O:34])[CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1446254-t-Amylbenzenesulphonyl chlorideHCID 58109960Ethyl 2-(3-amino-1-methylpiperidin-3-yl)acetate

Product 1

HCID 66865266Methyl 2-(1-methyl-3-(4-pentylphenylsulfonamido)piperidin-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of ethyl 2-(3-amino-1-methylpiperidin-3-yl)acetate (52 mg, 0.28 mmol) and triethylamine (0.2 mL, 1.44 mmol) in dichlormethane (15 mL) was treated with 4-n-pentylbenzenesulfonly chloride (120 mg, 0.487 mmol). The resulting mixture was stirred overnight. After removal of the volatiles, the residue was redissolved in dichloromethane, washed with sat. NaHCO3, dried (Na2SO4), evaporated and purified by flash chromatography (eluent: EtOAc/hex 1:1 to EtOAc) to give the title compound. (95 mg, 86%) as colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.80 (d, 2H, J=8.0 Hz), 7.27 (d, 2H, J=8.0 Hz), 5.67 (brs, 1H), 3.55 (s, 3H), 2.84 (d, 1H, J=11.6 Hz), 2.73-2.60 (m, 4H), 2.47 (brs, 1H), 2.20-1.92 (m, 6H; NCH3 and 3H), 1.70-1.57 (m, 3H), 1.48-1.27 (m, 6H), 0.88 (t, 3H, J=7.2 Hz); MS 397.2 ESI [M+H]+, calcd for [C20H32N2O4S+H]+ 397.22

Workup

  1. customAfter removal of the volatiles
  2. dissolutionthe residue was redissolved in dichloromethane
  3. washwashed with sat. NaHCO3
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. custompurified by flash chromatography (eluent: EtOAc/hex 1:1 to EtOAc)

Sources & evidence

ORD record
ord-881d44fc4c1745218aaa83cb9ee2e349
Source dataset
uspto-grants-2014_03
Patent number
US08680282B2

Reaction notes

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