Benzyl 4-(2-(dimethylamino)-2-oxoethoxy)piperidine-1-carboxylate → N,N-Dimethyl-2-(piperidin-4-yloxy)acetamide

HRID 1091763Notes

Reaction equation

HRID 1091763 reaction equation
[CH3:1][N:2]([CH3:23])[C:3](=[O:22])[CH2:4][O:5][CH:6]1[CH2:11][CH2:10][N:9](C(OCC2C=CC=CC=2)=O)[CH2:8][CH2:7]1>[Pd].C(O)C>[CH3:1][N:2]([CH3:23])[C:3](=[O:22])[CH2:4][O:5][CH:6]1[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]1

Participants

4

Reactant 1

HCID 57791803Benzyl 4-(2-(dimethylamino)-2-oxoethoxy)piperidine-1-carboxylate

Product 1

HCID 43346284N,N-Dimethyl-2-(piperidin-4-yloxy)acetamideYield 57.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl 4-(2-(dimethylamino)-2-oxoethoxy)piperidine-1-carboxylate (81) (3.0 g, 9.36 mmol) and palladium on carbon (0.100 g, 0.94 mmol) were added to ethanol (40 mL). This was stirred for 3 hours under an atmosphere of hydrogen. The reaction was filtered and the solvent evaporated to afford a viscous clear oil. The crude product was purified by distillation at 0.5 mBar, collecting fractions that distilled at 90° C. to afford the desired material as a colourless oil (1.000 g, 57.3% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.51-1.42 (2H, m), 1.98-1.92 (2H, m), 2.63-2.57 (2H, m), 2.95 (3H, s), 3.10-3.05 (5H, m), 3.51-3.44 (1H, m), 4.17 (2H, s) NH proton missing.

Workup

  1. filtrationThe reaction was filtered
  2. customthe solvent evaporated
  3. customto afford a viscous clear oil
  4. distillationThe crude product was purified by distillation at 0.5 mBar
  5. customcollecting fractions
  6. distillationthat distilled at 90° C.

Sources & evidence

ORD record
ord-7ebb4a077fd346c485ba3c9b3359d567
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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