Silica → Tert-butyl 4-[3-(acetylamino)phenyl]-1-piperidinecarboxylate

HRID 1832139Notes

Reaction equation

HRID 1832139 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:15][CH:16]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].O=[Si]=O>CCO.[Pd]>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 24261SilicaHCID 219571881,1-Dimethylethyl 4-[3-(acetylamino)phenyl]-3,6-dihydro-1(2H)-pyridinecarboxylate

Product 1

HCID 22049422Tert-butyl 4-[3-(acetylamino)phenyl]-1-piperidinecarboxylateYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture tert-butyl 4-[3-(acetylamino)phenyl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate (710 mg) and 5% Pd/C (100 mg) in EtOH (10 mL) was hydrogenated (balloon technique) at room temperature overnight. The reaction mixture was passed through a pad of Celite 545 and the pad of Celite was washed with ethanol. The combined ethanol extracts were concentrated and chromatograghed, giving the desired product (660 mg): 1H NMR (CDCl3) δ 7.80 (s, 1H), 7.41–7.20 (m, 3H), 6.94 (d, 1H, J=7.5 Hz), 4.21 (m, 2H), 2.75 (m, 2H), 2.62 (m, 1H), 2.16 (s, 3H), 1.78 (m, 2H), 1.56 (m, 2H), 1.48 (s, 9H).

Workup

  1. customat room temperature
  2. customovernight
  3. washthe pad of Celite was washed with ethanol
  4. concentrationThe combined ethanol extracts were concentrated

Sources & evidence

ORD record
ord-d217480fd87f4d04a726edcb6fc653b0
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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