Hydrochloric Acid → HCID 69075695, compound

HRID 1869732Notes

Reaction equation

HRID 1869732 reaction equation
C[O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH:6]=1.[ClH:22].[CH3:23]O>O=[Pt]=O>[ClH:22].[CH3:23][CH:4]([CH:5]1[CH2:10][CH2:9][NH:8][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH2:6]1)[C:3]([OH:2])=[O:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 46942028HCID 46942028, compound

Product 1

HCID 69075695HCID 69075695, compound

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

A mixture of methyl{2-[4-(trifluoromethyl)phenyl]pyridin-4-yl}acetate (6.2 g, 21 mmol), PtO2 (200 mg, 0.9 mmol) and HCl solution (4N in dioxane, 5.8 ml, 23 mmol) in MeOH (100 ml) was hydrogenated at 20 psi on a Parr® apparatus for 5 hours. The catalyst was removed by filtration and the filtrate evaporated in vacuo to give the desired piperidine as white solid (7.1 g, quant). 1H NMR (400 MHz, CD3OD) δ: 1.58-1.72 (1H, m), 1.75-1.85 (1H, m), 2.08 (1H, d, J 14.2), 2.19 (1H, t, J 14.2), 2.28-2.38 (1H, m), 2.45 (2H, d, J 6.9), 3.24-3.32 (1H, m), 3.51-3.57 (1H, m), 3.67 (3H, s), 4.46 (1H, d, J 10.2), 7.72 (2H, d, J 8.3), 7.79 (2H, d, J 8.4).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-5ac8e35a31a0493a8b3c0946914661b9
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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