Water → HCID 66761321, compound

HRID 876320Notes

Reaction equation

HRID 876320 reaction equation
[CH3:1][CH:2]([C:4]1[CH:5]=[C:6]([CH:10]2[CH2:15][NH:14][CH2:13][CH:12]([NH:16][C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:11]2)[CH:7]=[CH:8][CH:9]=1)[CH3:3].[N:25]1([C:31](Cl)=[O:32])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C(N(CC)CC)C.O>ClCCl>[N:25]1([C:31]([N:14]2[CH2:15][CH:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([CH:2]([CH3:1])[CH3:3])[CH:5]=3)[CH2:11][CH:12]([NH:16][C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[O:24])[CH2:13]2)=[O:32])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 66701303HCID 66701303, compound

Product 1

HCID 66761321HCID 66761321, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., 180 mg (0.54 mmol) of N-{5-[3-(1-methylethyl)phenyl]piperidin-3-yl}benzamide were initially charged in 4 ml of dichloromethane, and 162 mg (1.08 mmol) of morpholine-4-carbonyl chloride and 114 μl (0.81 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: 121 mg (51% 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-1ca4f6247590464ea5bebf52dec55075
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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