Chloride → 1-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-chloromethylindoline

HRID 1790456Notes

Reaction equation

HRID 1790456 reaction equation
CCN(S(F)(F)F)CC.[F:10][C:11]1[CH:35]=[CH:34][C:14]([CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[C:31]4[C:26](=[CH:27][CH:28]=[C:29]([CH2:32]O)[CH:30]=4)[CH2:25][CH2:24]3)[CH2:19][CH2:18]2)=[CH:13][CH:12]=1.[Cl-:36].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[F:10][C:11]1[CH:35]=[CH:34][C:14]([CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH:20]([N:23]3[C:31]4[C:26](=[CH:27][CH:28]=[C:29]([CH2:32][Cl:36])[CH:30]=4)[CH2:25][CH2:24]3)[CH2:19][CH2:18]2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 312ChlorideHCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 220378911-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-hydroxymethylindoline

Product 1

HCID 220382531-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-chloromethylindolineYield 30%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Diethylaminosulfatrifluoride (DAST, 160 mg) was added dropwise at −78° C. into a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-hydroxymethylindoline (300 mg) inmethylene chloride (10 ml) and the resultant mixture was stirred for 1 hr. Then a saturated aqueous solution of sodium bicarbonate and ethyl acetate were added thereto and the layers were separated. The organic layer was dried over anhydrous magnesium sulfate and the obtained residue was purified by NH-silica gel column chromatography (hexane/ethyl acetate system) followed by conversion into a hydrochloride in a conventional manner to give the hydrochloride (100 mg) of the title compound as a white powder (yield: 30%).

Workup

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

Sources & evidence

ORD record
ord-dbe8ac018eab4f28a8567ad116fe05d1
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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