5-Chloro-1-[1-[2-(indan-2-yl)ethyl]-1,2,3,6-tetrahydropyridin-4-yl]-1H-indole → 5-Chloro-1-[1-[2-(indan-2-yl)ethyl]piperidin-4-yl]-1H-indole

HRID 275722Notes

Reaction equation

HRID 275722 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]1[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH:19]3[CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20]3)[CH2:15][CH:16]=1)[CH:6]=[CH:5]2.[H][H]>[Pt]=O.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH:19]3[CH2:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[CH2:20]3)[CH2:15][CH2:16]1)[CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 185458365-Chloro-1-[1-[2-(indan-2-yl)ethyl]-1,2,3,6-tetrahydropyridin-4-yl]-1H-indole2×HCID 178418361HCID 178418361, compound

Product 1

HCID 185458415-Chloro-1-[1-[2-(indan-2-yl)ethyl]piperidin-4-yl]-1H-indole

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 5-Chloro-1-[1-[2-(indan-2-yl)ethyl]-1,2,3,6-tetrahydropyridin-4yl]-1H-indol. 28a. (1.9 g), acetic acid (50 ml), and platinum oxide (0.1 g) was shaken for 3 h under 3 atm. hydrogen pressure. The mixture was filtered and evaporated in vacuo. The residue was dissolved in ethyl acetate and the organic phase was shaken with dilute ammonium hydroxide and then worked up in a conventional manner. Further purification was done on silica gel eluted with ethyl acetate-heptane (1:1) to give 2.0 g of crude product. The crude product was crystallized (ethyl acetate), and the title compound was collected by filtration (1.1 g, 58%).

Workup

  1. filtrationThe mixture was filtered
  2. customevaporated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. customFurther purification
  5. washeluted with ethyl acetate-heptane (1:1)

Sources & evidence

ORD record
ord-54697a72aafd4e599ffd898a88433804
Source dataset
uspto-grants-2002_03
Patent number
US06352988B2

Reaction notes

Loading…