Triethylamine → 861151-12-4

HRID 221207Notes

Reaction equation

HRID 221207 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 11316914861151-12-4

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

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

Workup

  1. customwas -cooled to 0° C.
  2. customThe resulting reaction mixture
  3. washThe reaction mixture was washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness in a rotavapor
  7. customThe resulting crude solid was crystallised from ethanol
  8. customThe crystallised solid was removed via filtration
  9. concentrationthe mother liquors were concentrated
  10. customto yield a second fraction of crystallised product
  11. customto give

Sources & evidence

ORD record
ord-959ed1f655d6420faab0d131d8ab6c6d
Source dataset
uspto-grants-2012_06
Patent number
US08207156B2

Reaction notes

Loading…