Dimethylformamide → HCID 18507156, compound

HRID 1355566Notes

Reaction equation

HRID 1355566 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:27]2[CH:28]=[C:29](OS(C(F)(F)F)(=O)=O)[CH:30]=[CH:31][CH:32]=2)([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:26])[N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:41][N:42](C=O)C>C(OCC)C.[C-]#N.[Zn+2].[C-]#N>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])=[O:26])=[CH:18][CH:19]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:41]#[N:42])[CH:28]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 53786679HCID 53786679, compound

Product 1

HCID 18507156HCID 18507156, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of trifluoro-methanesulfonic acid 3-[1-benzyl-3-(4-diethylcarbamoyl-phenyl)-piperidin-3-yl]-phenyl ester (0.40 g, 0.69 mmol) in DMF (8 mL) was added zinc cyanide (0.057 g, 0.49 mmol) and tetrakis triphenylphosphine palladium (0.16 g, 0.14 mmol). The reaction was stirred under a nitrogen atmosphere at 90° C. for 5 hours. The mixture was cooled to room temperatures and it was diluted with diethyl ether (30 mL). The organic layer was washed with brine (5x 10 mL), dried (MgSO4) and concentrated. Purification with hexanes/EtOAc (1:1) afforded 0.28 g of 4-[1-benzyl-3-(3-cyano-phenyl)-piperidin-3-yl]-N,N-diethyl-benzamide. 1HNMR (400 MHz, CDCl3) δ 7.66 (s, 1H), 7.69-7.20 (comp, 10H), 7.15-7.13 (comp, 2H) 3.60-3.38 (comp, 4H), 3.31-3.19 (comp, 2H), 3.09-2.94 (m, 1H), 2.58-2.45 (comp, 2H), 2.22-2.17 (comp, 3H), 1.71-1.61 (m, 1H), 1.28-1.16 (comp, 3H), 1.17-1.08 (comp, 3H); MS (M+1) 452.2.

Workup

  1. temperatureThe mixture was cooled to room temperatures and it
  2. washThe organic layer was washed with brine (5x 10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification with hexanes/EtOAc (1:1)

Sources & evidence

ORD record
ord-54017badff0145cc9981d86f006733b7
Source dataset
uspto-grants-2003_07
Patent number
US06586431B1

Reaction notes

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