Piperidine → HCID 86605453, compound

HRID 1993565Notes

Reaction equation

HRID 1993565 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])=[CH:5][C:4]=1[C:16]([F:19])([F:18])[F:17].[NH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C(#N)C.O>[F:12][C:11]([F:14])([F:13])[C:10]([NH:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:5]=1)=[O:15]

Participants

5

Reactant 2

HCID 8082PiperidineHCID 57351764N-[4-(Bromomethyl)-3-(trifluoromethyl)phenyl]-2,2,2-trifluoroacetamide

Product 1

HCID 86605453HCID 86605453, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of N-(4-bromomethyl-3-trifluoromethyl-phenyl)-2,2,2-trifluoro-acetamide (Stage 128.3; 1.465 g, 4.19 mmol) in acetonitril (35 ml) under N2-atmosphere, piperidine (1.25 ml, 12.7 mmol) is added. After 30 min at rt the reaction mixture is diluted with water and partially concentrated in vacuo. The aqueous residue Is acidified to pH 5 by addition of 0.1 N HCl and extracted 3× with AcOEt. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Column chromatography (SiO2; hexane/AcOEt 3:2) gives the title compound: MS: [M+1]+=355; 1H-NMR (DMSO-d6): 11.48 (s, HN), 8.02 (s, 1H), 7.91 (dd, 1H), 7.77 (d, 1H), 3.52 (s, 2H), 2.32 (sb, 4H), 1.50 (m, 4H), 1.40 (m, 2H).

Workup

  1. concentrationpartially concentrated in vacuo
  2. additionThe aqueous residue Is acidified to pH 5 by addition of 0.1 N HCl
  3. extractionextracted 3× with AcOEt
  4. washThe organic layers are washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-72c91fe6a0924494a8e3bd3622264792
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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