HCID 89650329, compound → HCID 89650483, compound

HRID 1479026Notes

Reaction equation

HRID 1479026 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]=[C:11]1[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1>CO.C1COCC1.[Pd]>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH:11]1[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1

Participants

5

Reactant 1

HCID 89650329HCID 89650329, compound

Product 1

HCID 89650483HCID 89650483, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(1-methyl-piperidin-4-ylidenemethyl)-benzoic acid methyl ester (from Intermediate B12 step 1) (130 mg; 0.53 mmol; 1 eq.) and 10% Pd/C (˜50% H2O) (34 mg) in MeOH (1 mL) and THF (1 mL) was stirred at room temperature for 3 hours under a H2 atmosphere (10 bars). The catalyst was filtered off and the solution concentrated in vacuo. Purification by column chromatography (heptane/EA) afforded the title compound (97 mg, 74%) as a white solid. UPLC/MS: (MS+) 248.2 ([M+H]+).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe solution concentrated in vacuo
  3. customPurification by column chromatography (heptane/EA)

Sources & evidence

ORD record
ord-aac48ed665a64318825dcc4bf3e00dfd
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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