7-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole → 7-chloro-3-(piperidin-4-yl)-1H-indole

HRID 1779628Notes

Reaction equation

HRID 1779628 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=1.[H][H]>[Pt]=O.C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1

Participants

5

Reactant 2

HCID 185458497-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 178418361HCID 178418361, compound

Product 1

HCID 120720367-chloro-3-(piperidin-4-yl)-1H-indole

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

7-Chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (2.0 g, 8.62 mmol) and 0.5 g of platinum oxide were added to 100 mL of ethanol and the mixture was shaken under about 50 psi hydrogen at about ambient temperature for about a day. The mixture was filtered and the filtrate concentrated to yield a solid comprising the desired product. Yield 1.64 g (81%) as a yellow solid. FDMS m/e=234 (M+).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-b0c93f08d4a9400586571aae5014765e
Source dataset
uspto-grants-1997_05
Patent number
US05627196

Reaction notes

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