Triethylamine → 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-cyanoindoline

HRID 1790443Notes

Reaction equation

HRID 1790443 reaction equation
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[F:16][C:17]1[CH:42]=[CH:41][C:20]([CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([N:29]3[C:37]4[C:32](=[CH:33][CH:34]=[C:35]([CH:38]=[N:39]O)[CH:36]=4)[CH2:31][CH2:30]3)[CH2:25][CH2:24]2)=[CH:19][CH:18]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(Cl)(Cl)Cl>[F:16][C:17]1[CH:42]=[CH:41][C:20]([CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH:26]([N:29]3[C:37]4[C:32](=[CH:33][CH:34]=[C:35]([C:38]#[N:39])[CH:36]=4)[CH2:31][CH2:30]3)[CH2:27][CH2:28]2)=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 734445891-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-hydroxyiminomethylindoline

Product 1

HCID 110786031-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-cyanoindolineYield 70.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.72 ml) was added dropwise at −78° C. into a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-hydroxyiminomethylindoline (1.5 g) and triethylamine (1.2 ml) in methylene chloride (1 l) and the resultant mixture was warmed to room temperature. Next, a saturated aqueous solution of sodium bicarbonate and chloroform were added thereto and the layers were separated. The organic layer was dried over anhydrous magnesium sulfate and the residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (1.0 g) as a white powder (yield: 67%).

Workup

  1. customthe layers were separated
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-939df83e61034b7fb3378a75d1b9faaf
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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