Methanesulfonyl chloride → (r)-Methanesulfonic acid 3-[1-benzoyl-3-(3,4-dichloro-phenyl)-piperidin-3-yl]-propyl ester

HRID 394548Notes

Reaction equation

HRID 394548 reaction equation
C(N(C(C)C)CC)(C)C.[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2([CH2:32][CH2:33][CH2:34][OH:35])[CH2:23][CH2:22][CH2:21][N:20]([C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:25])[CH2:19]2)[CH:14]=[CH:15][C:16]=1[Cl:17].[CH3:36][S:37](Cl)(=[O:39])=[O:38]>C(Cl)Cl>[C:24]([N:20]1[CH2:21][CH2:22][CH2:23][C@@:18]([CH2:32][CH2:33][CH2:34][O:35][S:37]([CH3:36])(=[O:39])=[O:38])([C:13]2[CH:14]=[CH:15][C:16]([Cl:17])=[C:11]([Cl:10])[CH:12]=2)[CH2:19]1)(=[O:25])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 22741724[3-(3,4-Dichlorophenyl)-3-(3-hydroxy-propyl)-piperidin-1-yl]-phenyl-methanone

Product 1

HCID 15887657(r)-Methanesulfonic acid 3-[1-benzoyl-3-(3,4-dichloro-phenyl)-piperidin-3-yl]-propyl esterYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisopropylethylamine(1.6 mL, 9.18 mmol) was added to a solution of alcohol (10) (1.2 g, 3.06 mmol 3.0 eq) in CH2Cl2 (30 mL) followed by MsCl (0.28 mL, 3.67 mmol, 1.2 eq). The solution was stirred at room temperature for 2 hours, then quenched with water and diluted with CH2Cl2 (200 mL). The organic layer was washed with brine, 1N HCl, saturated NaHCO3, and dried over MgSO4. The crude oil was purified by flash chromatography (CH2Cl2-MeOH/95:5) to give light yellow solid (1.43 g, 99.3%).

Workup

  1. customquenched with water
  2. additiondiluted with CH2Cl2 (200 mL)
  3. washThe organic layer was washed with brine, 1N HCl, saturated NaHCO3
  4. dry with materialdried over MgSO4
  5. customThe crude oil was purified by flash chromatography (CH2Cl2-MeOH/95:5)

Sources & evidence

ORD record
ord-a7858e77998b40cb8f5bc5d9c6575e02
Source dataset
uspto-grants-2003_08
Patent number
US06602886B2

Reaction notes

Loading…