HCID 18511427, compound → HCID 18511415, compound

HRID 1370330Notes

Reaction equation

HRID 1370330 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([C:15]2[C:24]3[C:19](=[C:20]([C:25]([F:28])([F:27])[F:26])[CH:21]=[CH:22][CH:23]=3)[N:18]=[C:17]([C:29]([F:32])([F:31])[F:30])[CH:16]=2)([OH:14])[CH2:10][CH2:9]1)C1C=CC=CC=1>CO.[OH-].[Pd+2].[OH-]>[F:32][C:29]([F:30])([F:31])[C:17]1[CH:16]=[C:15]([C:11]2([OH:14])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[C:24]2[C:19](=[C:20]([C:25]([F:26])([F:27])[F:28])[CH:21]=[CH:22][CH:23]=2)[N:18]=1

Participants

4

Reactant 1

HCID 18511427HCID 18511427, compound

Product 1

HCID 18511415HCID 18511415, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-benzyl-4-(2,8-bis(trifluoromethyl)-4-quinolinyl)-4-piperidinol (480 mg, 1.06 mmol) and palladium hydroxide (100 mg) in MeOH (25 mL) was stirred vigorously under an atmosphere of hydrogen (using balloons) for 3 h, filtered through a pad of celite and concentrated in vacuo. The resulting viscous syrup was triturated with ether to give the title compound (241 mg, 63%) as a pale-grey solid: mp 210-220° C. (dec); IR νmax (Nujol)/cm−1 3406, 2924, 1458, 1313, 1154 and 823; NMR δH (400 MHz, DMSO-d6) 1.89 (2H, d, J 13.1 Hz), 2.11-2.19 (2H, m), 2.85 (2H, br d, J 10.0 Hz), 3.05-3.10 (2H, m), 5.73 (1H, s), 7.90 (1H, t, J 8.6 Hz), 8.03 (1H, s), 8.34 (1H, d, J 7.0 Hz) and 9.34 (1H, d, J 8.3 Hz).

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationconcentrated in vacuo
  3. customThe resulting viscous syrup was triturated with ether

Sources & evidence

ORD record
ord-2d3435a206634f7ea229eaf927524c39
Source dataset
uspto-grants-2003_06
Patent number
US06583156B1

Reaction notes

Loading…