Water → N-[5-(2,3-Dimethylphenyl)-1-(morpholin-4-ylcarbonyl)piperidin-3-yl]benzenecarboxamide

HRID 876321Notes

Reaction equation

HRID 876321 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][NH:13][CH2:12][CH:11]([NH:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10]1.[N:24]1([C:30](Cl)=[O:31])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C(N(CC)CC)C.O>ClCCl>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][N:13]([C:30]([N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)=[O:31])[CH2:12][CH:11]([NH:15][C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:23])[CH2:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 66701376N-[5-(2,3-dimethylphenyl)piperidin-3-yl]benzamide

Product 1

HCID 66701481N-[5-(2,3-Dimethylphenyl)-1-(morpholin-4-ylcarbonyl)piperidin-3-yl]benzenecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., 80 mg (0.26 mmol) of N-[5-(2,3-dimethylphenyl)piperidin-3-yl]benzamide were initially charged in 1.5 ml of dichloromethane, and 78 mg (0.52 mmol) of morpholine-4-carbonyl chloride and 55 μl (0.39 mmol) of triethylamine were added. The mixture was slowly warmed to RT overnight. Water was added, and the reaction mixture was extracted. The organic phase was dried over magnesium sulphate and concentrated under reduced pressure. The residue was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient). Yield: 75 mg (69% of theory)

Workup

  1. extractionthe reaction mixture was extracted
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was then purified by preparative HPLC (Reprosil C18, water/acetonitrile gradient)

Sources & evidence

ORD record
ord-737b2c10d8ef43b48a95bddde6d56dc9
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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