Water → N-{1-(Morpholin-4-ylcarbonyl)-5-[3-(trifluoromethyl)phenyl]piperidin-3-yl}benzenecarboxamide

HRID 876323Notes

Reaction equation

HRID 876323 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][NH:13][CH2:12][CH:11]([NH:15][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[N:26]1([C:32](Cl)=[O:33])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.C(N(CC)CC)C.O>ClCCl>[N:26]1([C:32]([N:13]2[CH2:14][CH:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:24])([F:1])[F:25])[CH:4]=3)[CH2:10][CH:11]([NH:15][C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:23])[CH2:12]2)=[O:33])[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 66701267N-{5-[3-(trifluoromethyl)phenyl]piperidin-3-yl}benzamide

Product 1

HCID 66701304N-{1-(Morpholin-4-ylcarbonyl)-5-[3-(trifluoromethyl)phenyl]piperidin-3-yl}benzenecarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., 165 mg (0.47 mmol) of N-{5-[3-(trifluoromethyl)phenyl]piperidin-3-yl}benzamide were initially charged in 17 ml of dichloromethane, and 71 mg (0.47 mmol) of morpholine-4-carbonyl chloride and 132 μl (0.95 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: 202 mg (92% 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-43d2da846e0d4d52a773aaff5977ca4c
Source dataset
uspto-grants-2015_03
Patent number
US08987248B2

Reaction notes

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