HCID 18407073, compound → 1,1-Dimethylethyl 4-(5-cyano-1H-indol-3-yl)-1-piperidinecarboxylate

HRID 1016497Notes

Reaction equation

HRID 1016497 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]#[N:24])[CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]#[N:24])[CH:21]=3)[NH:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 18407073HCID 18407073, compound

Product 1

HCID 184070691,1-Dimethylethyl 4-(5-cyano-1H-indol-3-yl)-1-piperidinecarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-[1-(t-butoxycarbonyl)-1,2,3,6-tetrahydro-pyridin-4-yl]-5-cyanoindole (15.3 g, 47.3 mmol) in ethanol was treated with 10% palladium on carbon (2.38 g). The mixture was hydrogenated on a Parr shaker at 50 psi for 18 hours and then filtered through celite to remove inorganics. Evaporation gave the desired product as an off white solid (15.2 g, 98%). 1H-NMR δ(CDCl3) 8.33 (br s, 1 H), 7.99 (s, 1 H), 7.42 (s, 2 H), 7.07 (s, 1 H), 4.22 (m, 2 H), 2.82 (m, 3 H), 1.98 (br d, 2 H), 1.66 (m, 2 H), 1.48 (s, 9 H).

Workup

  1. filtrationfiltered through celite
  2. customto remove inorganics
  3. customEvaporation

Sources & evidence

ORD record
ord-605ccc4efe5e4283a22d39b2061c81b4
Source dataset
uspto-grants-2002_11
Patent number
US06476051B2

Reaction notes

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