1-Benzyl-4-(N-tert-butoxycarbonyl-N-isopropylamino)piperidine → tert-butyl N-(piperidin-4-yl)-N-(propan-2-yl)carbamate

HRID 1181511Notes

Reaction equation

HRID 1181511 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:15]([CH3:17])[CH3:16])[CH2:10][CH2:9]1)C1C=CC=CC=1>C(O)C.[Pd]>[C:21]([O:20][C:18]([N:14]([CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[CH:15]([CH3:17])[CH3:16])=[O:19])([CH3:23])([CH3:24])[CH3:22]

Participants

4

Reactant 1

HCID 674284161-Benzyl-4-(N-tert-butoxycarbonyl-N-isopropylamino)piperidine

Product 1

HCID 50986573tert-butyl N-(piperidin-4-yl)-N-(propan-2-yl)carbamateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 1-benzyl-4-(N-tert-butoxycarbonyl-N-isopropylamino)piperidine (79.0 g, 0.24 mol) in ethanol (140 mL) was flushed with nitrogen for 15 minutes. This solution was then added to a 2 L Parr flask containing a mixture of 10% palladium on carbon (15.8 g; ca. 50% wt. water) in ethanol (100 mL), which solution had been flushed with nitrogen for 15 minutes. This reaction mixture was placed on a Parr Shaker under hydrogen at 50 psi for 24 hours. The reaction mixture was filtered through a pad of Celite and the Celite washed with ethanol. The filtrate was then concentrated in vacuo to afford 57.0 g of the title intermediate as a white solid (>99% yield).

Workup

  1. additionThis solution was then added to a 2 L Parr flask
  2. additioncontaining
  3. customhad been flushed with nitrogen for 15 minutes
  4. filtrationThe reaction mixture was filtered through a pad of Celite
  5. washthe Celite washed with ethanol
  6. concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record
ord-023f735e6bf5416ca0f2f4f3a198eb17
Source dataset
uspto-grants-2007_10
Patent number
US07285564B2

Reaction notes

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