Hydrochloric Acid → HCID 86597235, compound

HRID 1793445Notes

Reaction equation

HRID 1793445 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[N:8]=1)=[O:6].Cl>[Pt](=O)=O.C(O)C>[OH:1][CH2:2][CH2:3][NH:4][C:5]([CH:7]1[CH2:12][CH2:11][CH2:10][CH:9]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[NH:8]1)=[O:6]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86597234HCID 86597234, compound

Product 1

HCID 86597235HCID 86597235, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A quantity of 3.0 g (10 mmoles, 1 eq) of 6-(3,4-dimethoxy-phenyl)-pyridine-2-carboxylic acid (2-hydroxy-ethyl)-amide and 0.23 g (1.0 mmoles, 0.1 eq) of platinum dioxide are added into 35 mL of ethanol and 2.0 ml concentrated HCl. The suspension is hydrogenated under 50 psi of H2 at room temperature overnight. After TLC shows no starting material existing, the reaction is filtered through Celite and solvent is removed. The residue is taken in ethyl acetate, washed with saturated Na2CO3 and brine, dried over Na2SO4 and concentrated to give 6-(3,4-dimethoxy-phenyl)-piperidine-2-carboxylic acid (2-hydroxy-ethyl)-amide as a yellowish oil. The oil is triturated with ethyl acetate and hexanes to afford a white solid (1.6 g, 52%). Analysis: NMR (300 MHz, CDCl3): 7.18 (1H, t), 6.90 (2H, m), 6.82 (1H, m), 3.87 (6H, d), 3.66 (3H, m), 3.39 (3H, m), 2.00 (2H, m), 1.80 (1H, m) and 1.22 (2H, m). MS (LC-MS): Calculated for C16H24N2O4 308.37, found 309.34 (M+1).

Workup

  1. filtrationthe reaction is filtered through Celite and solvent
  2. customis removed
  3. washwashed with saturated Na2CO3 and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c0754a353ee9414ead2818ed353c537a
Source dataset
uspto-grants-2006_07
Patent number
US07081458B2

Reaction notes

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