Potassium Hydroxide → 1-Piperidin-4-yl-2,3-dihydro-1H-indole

HRID 580897Notes

Reaction equation

HRID 580897 reaction equation
[N:1]1([CH:10]2[CH2:15][CH2:14][N:13](C(OCC)=O)[CH2:12][CH2:11]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[K+]>CC(O)C>[NH:13]1[CH2:14][CH2:15][CH:10]([N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH2:2]2)[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 53677180HCID 53677180, compound

Product 1

HCID 220286031-Piperidin-4-yl-2,3-dihydro-1H-indoleYield 91.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of intermediate 6 (95 g) and potassium hydroxide (194 g) in 2-propanol (1300 ml) was stirred and refluxed for 24 hours. The solvent was evaporated and the residue was dissolved in H2O/CH2Cl2. The organic layer was separated, dried over MgSO4, filtered and evaporated, yielding 64 g (90.4%) of 2,3-dihydro-1-(4-piperidinyl)-1H-indole. A sample (4.5 g) was crystallized from CH3OH and converted into the hydrochloric acid salt (1:1) in 2-propanol and filtered off, yielding 3.0 g of 2,3-dihydro-1-(4-piperidinyl)-1H-indole monohydrochloride (intermediate 7).

Workup

  1. temperaturerefluxed for 24 hours
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in H2O/CH2Cl2
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-433927c8f7c644dc8ea16810f99615f2
Source dataset
uspto-grants-1999_07
Patent number
US05919788

Reaction notes

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