Triethylamine → HCID 131724114, compound

HRID 478374Notes

Reaction equation

HRID 478374 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C@H:10]2[CH2:15][CH2:14][NH:13][CH2:12][C@H:11]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:7][C:8]=1[Cl:9].C(N(CC)CC)C.[F:29][C:30]([F:45])([F:44])[C:31]1[CH:32]=[C:33]([CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=1)[C:34](Cl)=[O:35]>ClCCl.O>[F:29][C:30]([F:44])([F:45])[C:31]1[CH:32]=[C:33]([C:34]([N:13]2[CH2:14][CH2:15][C@H:10]([C:5]3[CH:6]=[CH:7][C:8]([Cl:9])=[C:3]([Cl:2])[CH:4]=3)[C@H:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12]2)=[O:35])[CH:37]=[C:38]([C:40]([F:41])([F:42])[F:43])[CH:39]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 1018563,5-Bis(trifluoromethyl)benzoyl chlorideHCID 14181122HCID 14181122, compound

Product 1

HCID 131724114HCID 131724114, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of rac-cis-4-(3,4-dichlorophenyl)-3-phenyl-piperidine hydrochloride (200 mg, 0.58 mmol) in 20 mL dichloromethane was added triethylamine (0.35 mL, 2.5 mmol) and 3,5-bistrifluoromethyl-benzoyl chloride (0.11 mL, 0.60 mmol). The reaction mixture was stirred at room temperature overnight and then diluted with 20 mL water. The organic phase was separated and the aqueous layer was extracted twice with 20 mL dichloromethane. Organic phases were pooled, dried with magnesium sulfate and evaporated. Recrystallization of the crude product from diisopropylether and hexanes gave the desired product (268 mg, 84%) as white crystalls, MS: m/e=546.1 (M+).

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous layer was extracted twice with 20 mL dichloromethane
  3. dry with materialdried with magnesium sulfate
  4. customevaporated
  5. customRecrystallization of the crude product from diisopropylether and hexanes

Sources & evidence

ORD record
ord-9df35511005645afb5487b5fa14679ab
Source dataset
uspto-grants-2003_11
Patent number
US06642226B2

Reaction notes

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