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

HRID 1790455Notes

Reaction equation

HRID 1790455 reaction equation
[ClH:1].[F:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([CH2:24]O)[CH:22]=4)[CH2:17][CH2:16]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[OH-].[Na+]>C(OCC)(=O)C>[F:2][C:3]1[CH:27]=[CH:26][C:6]([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([CH2:24][Cl:1])[CH:22]=4)[CH2:17][CH2:16]3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 220378911-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-hydroxymethylindoline

Product 1

HCID 220382531-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-chloromethylindolineYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Conc. hydrochloric acid (280 ml) was added to 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-hydroxymethylindoline (about 70 g) and the resultant mixture was stirred at 80° C. for a day. Under ice cooling, the reaction solution was neutralized with a conc. aqueous solution of sodium hydroxide followed by addition of ethyl acetate (200 ml). The resulting crystals were collected by filtration and dissolved in ethyl acetate (500 ml) and a 5 N aqueous solution (500 ml) of sodium hydroxide and the layers were separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (70 g) as a pale yellow powder (yield: 94%).

Workup

  1. filtrationThe resulting crystals were collected by filtration
  2. dissolutiondissolved in ethyl acetate (500 ml)
  3. customa 5 N aqueous solution (500 ml) of sodium hydroxide and the layers were separated
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7b4a5ba2bb0948feb754fedc653f46cb
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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