Water → 1-(Morpholin-4-ylcarbonyl)-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxamide

HRID 1642811Notes

Reaction equation

HRID 1642811 reaction equation
C(N(CC)CC)C.[N:8]1([C:14](Cl)=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.C(O)(=O)C.[F:21][C:22]([F:39])([F:38])[C:23]1[CH:28]=[CH:27][C:26]([CH:29]2[CH2:34][NH:33][CH2:32][CH:31]([C:35]([NH2:37])=[O:36])[CH2:30]2)=[CH:25][CH:24]=1.O>ClCCl>[N:8]1([C:14]([N:33]2[CH2:34][CH:29]([C:26]3[CH:25]=[CH:24][C:23]([C:22]([F:39])([F:38])[F:21])=[CH:28][CH:27]=3)[CH2:30][CH:31]([C:35]([NH2:37])=[O:36])[CH2:32]2)=[O:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 848104-Morpholinecarbonyl chlorideHCID 667551875-[4-(Trifluoromethyl)phenyl]piperidine-3-carboxamide acetate

Product 1

HCID 580024451-(Morpholin-4-ylcarbonyl)-5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., 0.56 g (5.52 mmol) of triethylamine and 0.55 g (3.70 mmol) of morpholine-4-carbonyl chloride were added to a solution of 0.61 mg (1.85 mmol) of 5-[4-(trifluoromethyl)phenyl]piperidine-3-carboxamide acetate (Example 51A) in 10 ml of dichloromethane. The reaction mixture was stirred at RT for 1 h. After addition of water and phase separation, the organic phase was dried over sodium sulphate, filtered and concentrated under reduced pressure. This gave 0.61 g (100% of theory) of crude product in a purity of 77% (LC-MS), which was reacted without any further purification steps.

Workup

  1. dry with materialthe organic phase was dried over sodium sulphate
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThis gave 0.61 g (100% of theory) of crude product in a purity of 77% (LC-MS), which was reacted without any further purification steps

Sources & evidence

ORD record
ord-b338b43ebd074d9cb6644ec3b97a0b2e
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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