HCID 66731519, compound → HCID 66731788, compound

HRID 1963189Notes

Reaction equation

HRID 1963189 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][N:19]=2)[C:13]([O:15][CH3:16])=[O:14])[CH:6]=[C:7]([Cl:9])[CH:8]=1>CO.[Pt](=O)=O>[ClH:2].[Cl:9][C:7]1[CH:6]=[C:5]([CH:10]2[CH2:11][CH:12]([C:13]([O:15][CH3:16])=[O:14])[CH2:17][CH2:18][NH:19]2)[CH:4]=[C:3]([Cl:2])[CH:8]=1

Participants

4

Reactant 1

HCID 66731519HCID 66731519, compound

Product 1

HCID 66731788HCID 66731788, compoundYield 136.9%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

Methyl 2-(3,5-dichlorophenyl)isonicotinate hydrochloride (6.88 g, 21.6 mmol) was dissolved in MeOH (50 mL), added platinum(IV) oxide (0.049 g, 0.22 mmol) and hydrogenated in a Büchi hydrogenator at 5 bar for 4 h. Reaction mixture filtered, washed with MeOH until all product had dissolved and evaporated. Methyl 2-(3,5-dichlorophenyl)piperidine-4-carboxylate hydrochloride (4.8 g, 69%) was isolated as a yellowish solid. MS m/z 288 (M+H)+

Workup

  1. customReaction mixture
  2. filtrationfiltered
  3. washwashed with MeOH until all product
  4. dissolutionhad dissolved
  5. customevaporated

Sources & evidence

ORD record
ord-a9ccb2c2f6a4416aa8e4a2496facde66
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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