5-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole → 4-(5-chloro-[1H]-indol-3-yl)-piperidine

HRID 351760Notes

Reaction equation

HRID 351760 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=1>C(O)(=O)C.O=[Pt]=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1

Participants

4

Reactant 1

HCID 30505325-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

Product 1

HCID 128313754-(5-chloro-[1H]-indol-3-yl)-piperidineYield 72.4%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

Crude 5-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole 8a (26 g) was dissolved in glacial acetic acid (330 ml) and PtO2 (0.7 g) was added. The mixture was hydrogenated in a Parr apparatus at 3 atm. for 5 hours. The catalyst was filtered off and excess acetic acid evaporated in vacuo. Water was added and pH was adjusted to >9 by addition of diluted aqueous NH4OH. Extraction with ethyl acetate (2×200 ml) and work-up of the combined organic phases yielded 19 g of crude title compound as a visceous oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. customexcess acetic acid evaporated in vacuo
  3. additionWater was added
  4. additionpH was adjusted to >9 by addition of diluted aqueous NH4OH
  5. extractionExtraction with ethyl acetate (2×200 ml)

Sources & evidence

ORD record
ord-d577a08f3d0a4d009fe0767cd7eaef52
Source dataset
uspto-grants-2004_06
Patent number
US06743808B1

Reaction notes

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