Triethylamine → 861151-12-4

HRID 2427127Notes

Reaction equation

HRID 2427127 reaction equation
[NH2:1][N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[N:26]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=3[Cl:34])[N:25]=[C:24]([C:35](Cl)=[O:36])[CH2:23]2)=[CH:18][CH:17]=1>C(Cl)Cl>[N:2]1([NH:1][C:35]([C:24]2[CH2:23][CH:22]([C:19]3[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=3)[N:26]([C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=3[Cl:34])[N:25]=2)=[O:36])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 166581-AminopiperidineHCID 25111746HCID 25111746, compound

Product 1

HCID 11316914861151-12-4Yield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Under nitrogen atmosphere N-aminopiperidine (0.6 mL, 5.6 mmoles) and triethylamine (4 mL) were dissolved in methylene chloride (25 mL). The resulting mixture was ice-cooled down to 0° C. and a solution of 5-(4-chlorophenyl-1-(2,4-dichlorophenyl)-4,5-dihydro-pyrazole-3carboxylic acid chloride obtained in step (c) in methylene chloride (15 mL) was added dropwise. The resulting reaction mixture was stirred at room temperature (approximately 25° C.) overnight. Afterwards the reaction mixture was washed with water, followed by a saturated aqueous solution of sodium bicarbonate, then again with water, dried over sodium sulfate, filtered and evaporated to dryness in a rotavapor. The resulting crude solid was crystallized from ethanol. The crystallized solid was removed via filtration and the mother liquors were concentrated to yield a second fraction of crystallized product. The two fractions were combined to give a total amount of 1.7 g (57% of theoretical yield) of N-piperidinyl-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydropyrazole-3-carboxamide having a melting point of 183-186° C.

Workup

  1. customThe resulting reaction mixture
  2. washAfterwards the reaction mixture was washed with water
  3. dry with materialagain with water, dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness in a rotavapor
  6. customThe resulting crude solid was crystallized from ethanol
  7. customThe crystallized solid was removed via filtration
  8. concentrationthe mother liquors were concentrated
  9. customto yield a second fraction of crystallized product

Sources & evidence

ORD record
ord-3da5b57ddd6d48b8bdf695b0e894b226
Source dataset
uspto-grants-2011_06
Patent number
US07968582B2

Reaction notes

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