Ethanol → Ethyl piperidin-4-ylmethoxyacetate, acetate salt

HRID 1900916Notes

Reaction equation

HRID 1900916 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][O:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C(O)C.[H][H]>[Pd].C(O)(=O)C>[C:20]([OH:22])(=[O:21])[CH3:19].[NH:11]1[CH2:16][CH2:15][CH:14]([CH2:17][O:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 702EthanolHCID 23370014ethyl N-(benzyloxycarbonyl)piperidin-4-ylmethoxyacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 131719663Ethyl piperidin-4-ylmethoxyacetate, acetate saltYield 201.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

In a similar manner to Example 2, starting material step (c), the product from step (a) (1.4 g), ethanol (100 ml), glacial acetic acid (0.25 g), 10% Pd on C (140 mg) and hydrogen gas were reacted to give ethyl piperidin-4-ylmethoxyacetate, acetate salt (1.1 g), as a brown oil: NMR Spectrum (DMSO-d6) 1.12 (2H, m), 1.20 (3H, t), 1.62 (3H, m), 1.84 (3H, s), 2.48 (2H, m), 2.96 (2H, m), 3.29 (2H, d), 4.05 (2H, s), 4.12 (2H, q).

Sources & evidence

ORD record
ord-4dcabb2e782742ecb0763e688d7c6d3d
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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