1H-Indole, 3-[1-(2-naphtho[1,2-b]furan-3-ylethyl)-4-piperidinyl]- → HCID 86595773, compound

HRID 1768026Notes

Reaction equation

HRID 1768026 reaction equation
[O:1]1[CH:5]=[C:4]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[NH:16][CH:15]=3)[CH2:10][CH2:9]2)[C:3]2[CH:23]=[CH:24][C:25]3[C:30]([C:2]1=2)=[CH:29][CH:28]=[CH:27][CH:26]=3>C(O)C.[Pd]>[O:1]1[CH:5]=[C:4]([CH2:6][CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[NH:16][CH:15]=3)[CH2:10][CH2:9]2)[C:3]2[CH:23]=[CH:24][C:25]3[C:30]([C:2]1=2)=[CH:29][CH:28]=[CH:27][CH:26]=3.[CH3:29][CH2:30][CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 1

HCID 112231571H-Indole, 3-[1-(2-naphtho[1,2-b]furan-3-ylethyl)-4-piperidinyl]-

Product 1

HCID 86595773HCID 86595773, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-{1-(2-naphtho[1,2-b]furan-3-yl-ethyl)-piperidin-4-yl]-1H-indole (197 mg, 0.5 mmol) obtained from step 6, was hydrogenated over 10% Pd/C in ethanol at 40 psi pressure. At the end, reaction mixture was filtered through a pad of celite and concentrated. The product obtained was purified by silica-gel column chromatography by eluting it with 70% ethyl acetate:hexane 3-{1-(2-naphtho[1,2-b]furan-3-yl-ethyl)-piperidin-4-yl]-1H-indole was isolated as yellow solid; Yield: 160 mg (81%); 395 (M+H); 1H NMR: δ 8.30 (1H, d, J=8 Hz), 7.99 (1H, s, NH), 7.94(1H, d, J=8 Hz), 7.67(4H, m), 7.58(1H, t, J=8 Hz), 7.48(1H, t, J=8 Hz), 7.38(1H, d, J=8 Hz), 7.20(1H, t, J=8 Hz), 7.13(1H, t, J=8 Hz), 7.0(1H, s), 3.21(2H, d, J=12 Hz), 3.04(1H, m), 2.90(1H, m), 2.84(2H, m), 2.29(2H, m), 2.13(2H, d, J=12 Hz), 1.90(2H, m, J=12 Hz).

Workup

  1. customAt the end, reaction mixture
  2. filtrationwas filtered through a pad of celite
  3. concentrationconcentrated
  4. customThe product obtained
  5. customwas purified by silica-gel column chromatography
  6. washby eluting it with 70% ethyl acetate

Sources & evidence

ORD record
ord-f7331bec5c494aaa8db87057782df104
Source dataset
uspto-grants-2007_06
Patent number
US07235569B2

Reaction notes

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