1H-Indole, 5-fluoro-3-(4-pyridinylmethyl)- → 5-fluoro-3-[(4-piperidinyl)methyl]-1H-indole

HRID 1166186Notes

Reaction equation

HRID 1166186 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1>C(O)C.C(O)(=O)C.O=[Pt]=O>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

5

Reactant 1

HCID 118169851H-Indole, 5-fluoro-3-(4-pyridinylmethyl)-

Product 1

HCID 112877165-fluoro-3-[(4-piperidinyl)methyl]-1H-indole

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 5-fluoro-3-(4-pyridinylmethyl)-1H-indole (4.50 g, 20 mmol) and PtO2 (0.50 g, 2.2 mmol) in ethanol and acetic acid is hydrogenated under 45 psi at room temperature for 48 hr. After filtration of the catalyst and concentration of the filtrate, the residue is taken up with water, basified to pH 11 with 1N NaOH and extracted with CH2Cl2/iPrOH (3/1). The combined extracts are dried over Na2SO4 and concentrated in vacuo to give a pink solid. The solid is crystallized from EtOAc to afford the title compound as a white solid, 4.0 g (86%) mp 155-157° C. (Lit. mp 163° C., Malleron et al, J. Med. Chem. 1193,36,1194).

Workup

  1. filtrationAfter filtration of the catalyst and concentration of the filtrate
  2. extractionextracted with CH2Cl2/iPrOH (3/1)
  3. dry with materialThe combined extracts are dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give a pink solid
  6. customThe solid is crystallized from EtOAc

Sources & evidence

ORD record
ord-1d50c4caf7c2445badd0924b5b6b2f20
Source dataset
uspto-grants-2003_09
Patent number
US06613781B2

Reaction notes

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