Methanesulfonyl chloride → (S)-N-{3-[4-({[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamino}methyl)piperidin-1-yl]-3-oxopropyl}methanesulfonamide

HRID 429833Notes

Reaction equation

HRID 429833 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][N:13]([C@@H:16]([CH3:27])[CH2:17][C:18]2[CH:19]=[CH:20][C:21]3[O:25][CH2:24][CH2:23][C:22]=3[CH:26]=2)[CH2:14][CH3:15])[CH2:8][CH2:7]1)=[O:5].C(N(C(C)C)CC)(C)C.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>ClCCl>[O:25]1[C:21]2[CH:20]=[CH:19][C:18]([CH2:17][C@@H:16]([N:13]([CH2:12][CH:9]3[CH2:10][CH2:11][N:6]([C:4](=[O:5])[CH2:3][CH2:2][NH:1][S:38]([CH3:37])(=[O:40])=[O:39])[CH2:7][CH2:8]3)[CH2:14][CH3:15])[CH3:27])=[CH:26][C:22]=2[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 54502007(S)-3-amino-1-[4-({[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamino}-methyl)piperidin-1-yl]propan-1-one

Product 1

HCID 54217577(S)-N-{3-[4-({[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamino}methyl)piperidin-1-yl]-3-oxopropyl}methanesulfonamideYield 66.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (S)-3-amino-1-[4-({[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamino}-methyl)piperidin-1-yl]propan-1-one (0.4 grams, 1.07 mmol) and diisopropylethylamine (0.21 grams, 1.62 mmole) in dichloromethane (10 ml) at 0° C. was added methanesulfonyl chloride (0.16 grams, 1.39 mmole). The reaction mixture was stirred at room temperature for 3 hours. The mixture was washed with water, dried over potassium carbonate and concentrated to give a residue which was purified by flash chromatography on silica gel using 3% methanol in dichloromethane containing 0.1% ammonium hydroxide. Appropriate fractions were combined and evaporated to give (S)-N-{3-[4-({[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]ethylamino}methyl)piperidin-1-yl]-3-oxopropyl}methanesulfonamide as an oil (0.32 grams, 66%), M+H 452. Analysis % of the hydrochloride salt: Found: C, 51.83; H, 7.38; N, 7.87. Requires: C, 51.82; H, 7.56; N, 7.88.

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried over potassium carbonate
  3. concentrationconcentrated
  4. customto give a residue which
  5. customwas purified by flash chromatography on silica gel using 3% methanol in dichloromethane containing 0.1% ammonium hydroxide
  6. customevaporated

Sources & evidence

ORD record
ord-8e1925d56bd44feba02f53eb55eb8b81
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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