Hydrochloric Acid → HCID 68480889, compound

HRID 2191124Notes

Reaction equation

HRID 2191124 reaction equation
C([N:8]1[CH2:13][C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[C:11]([C:21]([OH:23])=[O:22])[CH2:10][CH2:9]1)C1C=CC=CC=1.Cl.[CH3:25]O>[Pd]>[CH3:25][O:23][C:21]([CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH:12]1[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=[O:22]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid3×HCID 887Methanol3×HCID 23146847HCID 23146847, compound

Product 1

HCID 68480889HCID 68480889, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 3.6 g (1.03 mmol) 1-Benzyl-5-(4-fluoro-phenyl)-1,2,3,6-tetrahydro-pyridine-4-carboxylic acid (Bioorganic & Medicinal Chemistry Letters 2003, 2513-2518); hydrochloride, 16.6 mL HCl in methanol (1.25 N) in 250 mL methanol was stirred at room temperature over night. Further 16.6 mL HCl in methanol (1.25 N) was added and the mixture was stirred at 70° C. and subsequently hydrogenated with H2 over 360 mg Pd/C (10%) for 44 h at room temperature. The mixture was filtered off and evaporated to dryness to yield 2.3 g (94%) of the title compound as colorless oil. MS (m/e): 238.1 [(M+H)+].

Workup

  1. filtrationThe mixture was filtered off
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-859666a7a49f4297a15c7520d1b4f6bd
Source dataset
uspto-grants-2012_12
Patent number
US08324248B2

Reaction notes

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