HCID 69217729, compound → HCID 69217766, compound

HRID 269477Notes

Reaction equation

HRID 269477 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(OCC2C=CC=CC=2)=O)=[CH:4][C:3]=1[CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]3[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=3[F:41])=[CH:28][CH:27]=2)[CH2:21][CH2:20]1>C(O)C.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[CH:19]1[CH2:20][CH2:21][N:22]([CH2:25][C:26]2[CH:27]=[CH:28][C:29]([O:32][C:33]3[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=3[F:41])=[CH:30][CH:31]=2)[CH2:23][CH2:24]1

Participants

4

Reactant 1

HCID 69217729HCID 69217729, compound

Product 1

HCID 69217766HCID 69217766, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-[4-methyl-3-(1-{[4-(2,4,5-trifluorophenoxy)phenyl]methyl}(4-piperidyl))phenyl](phenylmethoxy)carboxamide (4.88 g, 8.68 mmol) was dissolved in ethanol (150 mL) and hydrogenated over palladium on carbon (10%, 980 mg) for 2.5 h. The reaction mixture was filtered through celite filter aid, washing with ethanol and the filtrate was concentrated in vacuo. Flash column chromatography (silica gel 60) eluting with cyclohexane:ethyl acetate (1:1 then 1:4) provided 4-methyl-3-(1-{[4-(2,4,5-trifluorophenoxy)phenyl]methyl}(4-piperidyl))phenylamine (3.71 g, 100%). LCMS (method B): 2.14 min, 427.0 (M+H)+; 1H NMR (400 MHz, CD3OD) δ 7.63 (d, 2H, J=7.2 Hz), 7.41-7.33 (m, 2H), 7.27-7.23 (m, 2H), 7.15 (d, 1H, J=8.0 Hz), 7.09 (d, 2H, J=8.0 Hz), 4.36 (s, 2H), 3.61 (d, 2H, J=12.0 Hz), 3.22 (t, 3H, J=12.0 Hz), 2.42 (s, 3H), 2.15-2.02 (m, 4H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. filtrationfilter aid
  3. washwashing with ethanol
  4. concentrationthe filtrate was concentrated in vacuo
  5. washFlash column chromatography (silica gel 60) eluting with cyclohexane:ethyl acetate (1:1

Sources & evidence

ORD record
ord-60e2449fee21401daebf5194f8437193
Source dataset
uspto-grants-2008_11
Patent number
US07446204B2

Reaction notes

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