Methanol → HCID 58659460, compound

HRID 1993564Notes

Reaction equation

HRID 1993564 reaction equation
FC(F)(F)C([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[C:8]([C:19]([F:22])([F:21])[F:20])[CH:7]=1)=O.CO.C([O-])([O-])=O.[K+].[K+]>O>[F:22][C:19]([F:20])([F:21])[C:8]1[CH:7]=[C:6]([NH2:5])[CH:11]=[CH:10][C:9]=1[CH2:12][N:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 86605453HCID 86605453, compound

Product 1

HCID 58659460HCID 58659460, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2,2,2-trifluoro-N-(4-piperidin-1-ylmethyl-3-trifluoromethyl-phenyl)-acetamide (Stage 128.2; 1.427 g, 4.03 mmol) in boiling methanol (42 ml), 20 ml of a 1 N solution of K2CO3 in water are added dropwise. After 2 h stirring, the reaction mixture is cooled to rt, concentrated in vacuo and the residue re-dissolved in AcOEt and water. The aqueous layer is separated off and extracted twice with AcOEt. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated to yield the title compound: MS: [M+1]+=259; 1H-NMR (DMSO-d6): 7.28 (d, 1H), 6.82 (d, 1H), 7.73 (dd, 1H), 5.40 (s, H2N), 3.32 (s, 2H), 2.27 (sb, 4H), 1.46 (m, 4H), 1.39 (m, 2H).

Workup

  1. additionare added dropwise
  2. concentrationconcentrated in vacuo
  3. dissolutionthe residue re-dissolved in AcOEt
  4. customThe aqueous layer is separated off
  5. extractionextracted twice with AcOEt
  6. washThe organic phases are washed with water and brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9105b905656244ef8ed4a6537d5c6cf4
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

Loading…