Methyl 5-[4-(2-hydroxyethyl)phenyl]nicotinate → Methyl 5-[4-(2-hydroxyethyl)phenyl]piperidine-3-carboxylate

HRID 2091778Notes

Reaction equation

HRID 2091778 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[C:14]([CH:19]=2)[C:15]([O:17][CH3:18])=[O:16])=[CH:6][CH:5]=1.[H][H]>C(O)(=O)C.[Pd].[Pt](=O)=O>[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:11][NH:12][CH2:13][CH:14]([C:15]([O:17][CH3:18])=[O:16])[CH2:19]2)=[CH:8][CH:9]=1

Participants

6

Reactant 2

HCID 59606586Methyl 5-[4-(2-hydroxyethyl)phenyl]nicotinateHCID 178418361HCID 178418361, compound

Product 1

HCID 59606575Methyl 5-[4-(2-hydroxyethyl)phenyl]piperidine-3-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalyst2×HCID 345198Adams' catalystCatalyst2×HCID 176Acetic AcidSolvent

Procedure

A solution of 5.40 g (19.6 mmol) of the compound from Example 55A in concentrated acetic acid (124 ml) was admixed with 1.00 g of palladium/carbon (10% palladium) and 1.00 g of platinum(IV) oxide. This was followed by hydrogenation under a hydrogen atmosphere at standard pressure for 6 h, then addition of another 1.00 g of palladium/carbon (10% palladium) and 1.00 g of platinum(IV) oxide, and hydrogenation under a hydrogen atmosphere at standard pressure overnight. This was followed by hydrogenation in a Pan apparatus under a 3 bar hydrogen atmosphere for a further 2 h. The reaction solution was filtered through Celite, the filter residue was washed with methanol/water and the combined filtrates were concentrated under reduced pressure. The residue was codistilled repeatedly with toluene and then dried under high vacuum. Yield: 6.63 g (56% of theory, purity 44%)

Workup

  1. filtrationThe reaction solution was filtered through Celite
  2. washthe filter residue was washed with methanol/water
  3. concentrationthe combined filtrates were concentrated under reduced pressure
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-ea4fe50ede1344e692e42e52587af823
Source dataset
uspto-grants-2013_05
Patent number
US08440657B2

Reaction notes

Loading…