HCID 12229248, compound → 3-(1-Methyl-4-piperidinyl)-1H-indol-5-ol

HRID 1766229Notes

Reaction equation

HRID 1766229 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[C:12]2[C:18]1[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH:23]=1)C1C=CC=CC=1.[H][H]>[Pd].C(O)C.O1CCCC1>[CH3:24][N:21]1[CH2:20][CH2:19][CH:18]([C:12]2[C:11]3[C:15](=[CH:16][CH:17]=[C:9]([OH:8])[CH:10]=3)[NH:14][CH:13]=2)[CH2:23][CH2:22]1

Participants

6

Reactant 2

HCID 12229248HCID 12229248, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 24383-(1-Methyl-4-piperidinyl)-1H-indol-5-olYield 51.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-benzyloxy-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole (16.4 g, 51.5 mmol) and 5% palladium on carbon (4.0 g) in ethanol (125 mL) and tetrahydrofuran (125 mL) was hydrogenated with an initial hydrogen pressure of 60 psi (413 kPa) at ambient temperature for 16 h. The reaction mixture was filtered and concentrated under reduced pressure. The residue was crystallized from methanol and THF to give 6.06 g (51%) of the title compound as white crystals: mp=234-237° C.; MS(m/e): 230 (M+); Calculated for C14H18N2O: Calcd: C, 73.01; H, 7.88; N, 12.16. Found: C, 72.79; H, 8.17; N, 12.33.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was crystallized from methanol and THF

Sources & evidence

ORD record
ord-690da6f168794e6d889ea9a1b7bc15c5
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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