Trifluoroacetic acid → HCID 59548735, compound

HRID 1810976Notes

Reaction equation

HRID 1810976 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[NH:21][C:22](=[O:30])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[Cl:29][C:25]1[CH:24]=[C:23]([CH:28]=[CH:27][CH:26]=1)[C:22]([NH:21][C:15]1[CH:16]=[C:17]([Cl:20])[CH:18]=[CH:19][C:14]=1[C:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=1)=[O:30]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 59548904HCID 59548904, compound

Product 1

HCID 59548735HCID 59548735, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of 4-[4-chloro-2-(3-chloro-benzoylamino)-phenyl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.504 g, 1.13 mmol) in dichloromethane (10 mL) is added trifluoroacetic acid (1 mL) in a dropwise fashion. The resulting reaction is allowed to stir at room temperature for 2 h. 2N NaOH aqueous solution is added to adjust the pH>12. The mixture is then extracted with dichloromethane 3×. The organic layers are combined, washed with brine 1×, dried (Na2SO4) and concentrated under vacuum to give 0.391 g of 3-chloro-N-[5-chloro-2-(1,2,3,6-tetrahydro-pyridin-4-yl)-phenyl]-benzamide in 99% yield.

Workup

  1. customThe resulting reaction
  2. extractionThe mixture is then extracted with dichloromethane 3×
  3. washwashed with brine 1×
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c2bd247645f949888031fa368e1d1a31
Source dataset
uspto-grants-2013_01
Patent number
US08362249B2

Reaction notes

Loading…