HCID 57565327, compound → HCID 57565333, compound

HRID 2110120Notes

Reaction equation

HRID 2110120 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][N:15]=2)[C@H:10]([CH3:24])[CH2:9]1)C1C=CC=CC=1>C(O)C.[Pd]>[CH3:24][C@@H:10]1[CH2:9][NH:8][CH2:13][CH2:12][N:11]1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:16][N:15]=1

Participants

4

Reactant 1

HCID 57565327HCID 57565327, compound

Product 1

HCID 57565333HCID 57565333, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-benzyl-2-(R)-methyl-1-(5-trifluoromethyl-pyridin-2-yl)-piperazine (175 mg, 0.522 mmol) and 10% Pd/C (cat) in ethanol (5 mL) was stirred under a hydrogen atmosphere (50 psi) for 3 d. The reaction mixture was then filtered through Celite and purified by silica gel column chromatography (gradient eluent: 0-20% MeOH in dichloromethane) to provide the desired product (117 mg, 99%). 1H NMR (400 MHz, MeOH-D4) δ 8.39 (s, 1H), 7.60 (dd, 1H), 7.39-7.28 (m, 5H), 6.58 (d, 1H), 4.49 (br s, 1H), 4.10 (br d, 1H), 3.62 (br d, 1H), 3.47 (br d, 1H), 3.24 (br t, 1H), 2.95 (br d, 1H), 2.77 (br d, 1H), 2.35-2.15 (m, 2H), 1.25 (d, 3H); LCMS: 246.1 (M+1)+.

Workup

  1. filtrationThe reaction mixture was then filtered through Celite
  2. custompurified by silica gel column chromatography (gradient eluent: 0-20% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-2feb583092194ec7a558e4cfecc3eb4d
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

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