Dimethylformamide → HCID 22729904, compound

HRID 2085458Notes

Reaction equation

HRID 2085458 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([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)[CH2:10][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][C:11]([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)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 53944364HCID 53944364, compound

Product 1

HCID 22729904HCID 22729904, compoundYield 91%

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-4-(4-diethylcarbamoyl-phenyl)-piperidin-4-yl]-phenyl ester (1.82 g, 3.16 mmol) in DMF (14 mL) was added zinc cyanide (0.26 g, 2.21 mmol) and tetrakis triphenylphosphine palladium (0.73 g, 0.63 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 (100 mL). The organic layer was washed with brine (5×10 mL), dried (MgSO4) and concentrated. Purification with hexanes/EtOAc (1:1) afforded 1.3 g (91% yield) of 4-[1-Benzyl-4-(3-cyano-phenyl)-piperidin-4-yl]-N,N-diethyl-benzamide. 1HNMR (400 MHz, CDCl3) δ 7.69-7.20 (comp, 13H), 3.55-3.43 (comp, 2H), 3.41 (s, 2H), 3.31-3.19 (comp, 2H), 2.6-2.25 (comp, 8H), 1.28-1.19 (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 (5×10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification with hexanes/EtOAc (1:1)

Sources & evidence

ORD record
ord-692d146cf40046a8b7a83ec17230759d
Source dataset
uspto-grants-2004_04
Patent number
US06720336B2

Reaction notes

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