Triethylamine → 4-[4-(2-Oxazolin-2-yl)benzylidene]-1-(4-trifluoromethylbenzoyl)piperidine

HRID 129089Notes

Reaction equation

HRID 129089 reaction equation
[O:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:18]=[CH:17][C:9]([CH:10]=[C:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:8][CH:7]=1.C(N(CC)CC)C.[F:26][C:27]([F:38])([F:37])[C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][CH:29]=1>C(OCC)(=O)C.C(Cl)Cl>[O:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]([CH:10]=[C:11]2[CH2:12][CH2:13][N:14]([C:32](=[O:33])[C:31]3[CH:35]=[CH:36][C:28]([C:27]([F:26])([F:37])[F:38])=[CH:29][CH:30]=3)[CH2:15][CH2:16]2)=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 676074-(Trifluoromethyl)benzoyl chlorideHCID 152314034-[4-(2-Oxazolin-2-yl)benzylidene]piperidine

Product 1

HCID 152313864-[4-(2-Oxazolin-2-yl)benzylidene]-1-(4-trifluoromethylbenzoyl)piperidine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

120 mg (0.5 mmol) of 4-[4-(2-oxazolin-2-yl)benzylidene]piperidine and 75 mg (0.75 mmol) of triethylamine in 3 ml of ethyl acetate and 2 ml of methylene chloride are cooled to -5° to -10° C. and 104.3 mg (0.5 mmol) of 4-trifluoromethylbenzoyl chloride are added. The mixture is stirred at ambient temperature for 1.5 hours, diluted with ethyl acetate, washed successively with water, 2N sodium hydroxide solution and saturated saline solution, dried and evaporated down. 115 mg (56% of theory) of the title compound of melting point 142° C. are obtained.

Workup

  1. washwashed successively with water, 2N sodium hydroxide solution and saturated saline solution
  2. customdried
  3. customevaporated down

Sources & evidence

ORD record
ord-3895126c1b6c4938850e9278ca15b188
Source dataset
uspto-grants-1995_11
Patent number
US05466687

Reaction notes

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