Hydrochloric Acid → HCID 22038128, compound

HRID 1790406Notes

Reaction equation

HRID 1790406 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.Cl>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][CH:13]([N:16]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH2:18][CH2:17]3)[CH2:14][CH2:15]2)=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22038173HCID 22038173, compound

Product 1

HCID 22038128HCID 22038128, compoundYield 0.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-[1-(4-Nitrophenethyl)piperidin-4-yl]indoline (780 g) was dissolved in methanol (7 ml) and conc. hydrochloric acid (0.5 ml) was added dropwise into the resultant solution. Subsequently, the resultant mixture was catalytically reduced under atmospheric pressure in the presence of a palladium catalyst. After filtering off the catalyst, a 1 N aqueous solution of sodium hydroxide was added to the filtrate followed by extraction with chloroform. The organic layer was washed with brine and dried over magnesium sulfate. After evaporating the solvent, the title compound (620 mg) was obtained as an oil.

Workup

  1. filtrationAfter filtering off the catalyst
  2. additiona 1 N aqueous solution of sodium hydroxide was added to the filtrate
  3. extractionfollowed by extraction with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporating the solvent

Sources & evidence

ORD record
ord-dd5bb6d2163d4851b2305b4614d03792
Source dataset
uspto-grants-2006_07
Patent number
US07071201B2

Reaction notes

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