(2-Chloro-4-trifluoromethyl-phenoxy)-acetic acid → n-{3-Chloro-4-[2-(4-methyl-piperidin-1-yl)-ethyl]-phenyl}-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide

HRID 898633Notes

Reaction equation

HRID 898633 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[Cl:17][C:18]1[CH:19]=[C:20]([NH2:33])[CH:21]=[CH:22][C:23]=1[CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][CH:29]([CH3:32])[CH2:28][CH2:27]1>>[Cl:17][C:18]1[CH:19]=[C:20]([NH:33][C:6](=[O:8])[CH2:5][O:4][C:3]2[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:2]=2[Cl:1])[CH:21]=[CH:22][C:23]=1[CH2:24][CH2:25][N:26]1[CH2:27][CH2:28][CH:29]([CH3:32])[CH2:30][CH2:31]1

Participants

3

Reactant 2

HCID 59691547(2-Chloro-4-trifluoromethyl-phenoxy)-acetic acidHCID 596916703-Chloro-4-[2-(4-methylpiperidin-1-yl)ethyl]phenylamine

Product 1

HCID 10074263n-{3-Chloro-4-[2-(4-methyl-piperidin-1-yl)-ethyl]-phenyl}-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide

Procedure

Prepared analogously to Example 143 starting from (2-chloro-4-trifluoromethyl-phenoxy)-acetic acid (Z2b) and 3-chloro-4-[2-(4-methyl-piperidin-1-yl )-ethyl]-phenylamine (Z46c). The reaction mixture was poured onto ice water and the aqueous phase was extracted with EtOAc. The org. phase was dried over sodium sulphate and evaporated down i. vac. The residue was purified by column chromatography (Alox, neutral, act. II-III, gradient petroleum ether/EtOAc 3:1→1:1).

Workup

  1. additionThe reaction mixture was poured onto ice water
  2. extractionthe aqueous phase was extracted with EtOAc
  3. dry with materialphase was dried over sodium sulphate
  4. customevaporated down i
  5. customThe residue was purified by column chromatography (Alox, neutral, act. II-III, gradient petroleum ether/EtOAc 3:1→1:1)

Sources & evidence

ORD record
ord-ef801e24dda44504afc42149b493bb10
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

Loading…