Water → HCID 86629751, compound

HRID 1510233Notes

Reaction equation

HRID 1510233 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[CH:10]([OH:18])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31].O>ClCCl.O1CCCC1.CN(C)C1C=CN=CC=1>[CH3:29][S:30]([O:18][CH:10]([CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)=[O:19])(=[O:32])=[O:31]

Participants

8

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 69080060HCID 69080060, compound

Product 1

HCID 86629751HCID 86629751, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-bromophenyl)-2-hydroxy-3-phenylpropanamide (1.5 g) in dichloromethane (60 mL) and tetrahydrofuran (30 mL) were added diisopropylethylamine (908 mg) and 4-dimethylaminopyridine (114 mg), followed by dropwise addition of methanesulfonyl chloride (805 mg) at 5° C. and the mixture was stirred at ambient temperature for 20 hours. The mixture was poured into water and concentrated in vacuo. The residue was extracted with ethyl acetate, washed with brine, dried over magnesium sulfate, and evaporated in vacuo to afford crude 1-benzyl-2-[(4-bromophenyl)amino]-2-oxoethyl methanesulfonate. The crude methanesulfonate was dissolved in N,N-dimethylformamide (30 mL) and 4-piperidinol (1.19 g) was added. The mixture was stirred at 80° C. for 5 hours and poured into water. The mixture was extracted with ethyl acetate, washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with ethyl acetate to afford N-(4-bromophenyl)-2-(4-hydroxypiperidin-1-yl)-3-phenylpropanamide (894 mg) as a powder.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe residue was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-2f805dfa806748dba85eedd7d6980928
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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