2-Chlorobenzenesulfonyl chloride → 2-chloro-N-{1-[(4-methylpiperidin-1-yl)carbonyl]-3-phenylpropyl}benzenesulfonamide

HRID 537391Notes

Reaction equation

HRID 537391 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8](=[O:19])[CH:9]([NH2:18])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][CH2:3]1.[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27](Cl)(=[O:29])=[O:28].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[S:27]([NH:18][CH:9]([C:8]([N:5]1[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH2:4]1)=[O:19])[CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 761872-Chlorobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 66997562HCID 66997562, compound

Product 1

HCID 585048692-chloro-N-{1-[(4-methylpiperidin-1-yl)carbonyl]-3-phenylpropyl}benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 29 mg (0.11 mmol) of 1-(4-methylpiperidin-1-yl)-1-oxo-4-phenylbutan-2-amine, 2-chlorobenzenesulfonyl chloride, and 0.19 mL (0.11 mmol) of iPr2NEt in 4 mL of CH2Cl2 is stirred for 16 h, concentrated, and purified by preparative HPLC to provide Example 1

Workup

  1. concentrationconcentrated
  2. custompurified by preparative HPLC
  3. customto provide Example 1

Sources & evidence

ORD record
ord-bdcee84947504fc8a58484f8b899e073
Source dataset
uspto-grants-2014_10
Patent number
US08859814B2

Reaction notes

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