Potassium Hydroxide → 1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinecarbonitrile

HRID 238668

Reaktionsgleichung

Reaktionsgleichung von HRID 238668
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]([F:10])([F:9])[F:8])[NH:4][N:3]=1.[OH-].[K+].Cl[CH2:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([C:23]#[N:24])[CH2:19][CH2:18]1)=[O:16]>CN(C)C=O.O>[CH3:1][C:2]1[N:3]([CH2:14][C:15]([N:17]2[CH2:18][CH2:19][CH:20]([C:23]#[N:24])[CH2:21][CH2:22]2)=[O:16])[N:4]=[C:5]([C:7]([F:10])([F:9])[F:8])[CH:6]=1

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 1390771H-Pyrazole, 3-methyl-5-(trifluoromethyl)-HCID 674700971-(2-Chloroacetyl)piperidine-4-carbonitrile2×

Produkt 1

HCID 674706371-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
7.5 °C

Versuchsvorschrift

A solution of 3-methyl-5-trifluoromethylpyrazole (9.3 g, 62 mmol) and 45% aqueous potassium hydroxide solution (7.79 g, 62 mmol) in N,N-dimethylformamide (25 mL) was cooled to 5° C., and 1-(2-chloroacetyl)-4-piperidinecarbonitrile (i.e. the product of Example 8, Step A or A1) (11.2 g, 60 mmol) was added. The reaction mixture was stirred for 8 h at 5-10° C., then diluted with water (100 mL), and filtered. The filter cake was washed with water and dried at 50° C. in a vacuum-oven to give 15 g of the title compound as a solid containing 3% of its regioisomer, i.e. 1-[2-[3-methyl-5-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinecarbonitrile.

Aufarbeitung

  1. filtrationfiltered
  2. washThe filter cake was washed with water
  3. customdried at 50° C. in a vacuum-oven

Quellen und Nachweise

ORD-Eintrag
ord-3cb205934601414d8db1b645cc1d22b7
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642634B2

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