6-[4-(1-Benzyl-1,2,5,6-tetrahydro-pyridin-3-yl)-phenoxy]-nicotinamide hydrochloride salt → (+/-)-6-(4-Piperidin-3-yl-phenoxy)-nicotinamide hydrochloride

HRID 130744Notes

Reaction equation

HRID 130744 reaction equation
[ClH:1].C([N:9]1[CH2:14][CH2:13][CH:12]=[C:11]([C:15]2[CH:30]=[CH:29][C:18]([O:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[O:25])=[CH:22][N:21]=3)=[CH:17][CH:16]=2)[CH2:10]1)C1C=CC=CC=1>[Pd].CO>[ClH:1].[NH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]2[CH:16]=[CH:17][C:18]([O:19][C:20]3[CH:28]=[CH:27][C:23]([C:24]([NH2:26])=[O:25])=[CH:22][N:21]=3)=[CH:29][CH:30]=2)[CH2:10]1

Participants

4

Reactant 1

HCID 687513806-[4-(1-Benzyl-1,2,5,6-tetrahydro-pyridin-3-yl)-phenoxy]-nicotinamide hydrochloride salt

Product 1

HCID 68747046(+/-)-6-(4-Piperidin-3-yl-phenoxy)-nicotinamide hydrochlorideYield 39%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Combine the product of example 321 (0.0421 g, 0.0998 mmol), 10% Pd—C (2 spatula tips), and methanol (2.0 mL). Bubble one balloon of hydrogen gas through solution then stir under ca. 1 atm. After 3.5 h, filter the reaction mixture through Celite®, concentrate, and purify by reverse-phase HPLC to provide 0.0129 g (39%) of the title compound as a white solid: mass spectrum (electrospray): m/z=298.1 (M+1); 1H NMR (methanol-d4): 8.86 (s br, 1H), 8.59 (dd, 1H, J=2.0, 8.8 Hz), 7.53 (d, 2H, J=8.3 Hz), 7.32 (d, 2H, J=7.8 Hz), 7.19 (d, 1H, J=8.8 Hz), 3.51 (d, 1H, J=8.3 Hz), 3.25-3.08 (m, 3H), 2.18-2.08 (m, 2H), 2.06-1.84 (m, 2H).

Workup

  1. customBubble one balloon of hydrogen gas through solution
  2. filtrationfilter the reaction mixture through Celite®
  3. concentrationconcentrate
  4. custompurify by reverse-phase HPLC

Sources & evidence

ORD record
ord-eeed164eda3d4e8180043bb80dc01311
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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