Ethanol → Ethyl piperidin-4-yloxyacetate, acetate salt

HRID 1900912Notes

Reaction equation

HRID 1900912 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([O:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C(O)C.[H][H]>[Pd].C(O)(=O)C>[C:19]([OH:21])(=[O:20])[CH3:18].[NH:11]1[CH2:12][CH2:13][CH:14]([O:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:15][CH2:16]1

Participants

6

Reactant 3

HCID 702EthanolHCID 23370004Ethyl 1-benzyloxycarbonylpiperidine-4-oxyacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 131719662Ethyl piperidin-4-yloxyacetate, acetate saltYield 192.1%

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) (2.3 g), ethanol (200 ml), glacial acetic acid (0.6 ml), 10% Pd on C (200 mg) and hydrogen gas were reacted to give ethyl piperidin-4-yloxyacetate, acetate salt (1.7 g), as a brown oil: NMR Spectrum (DMSO-d6) 1.20 (3H, t), 1.41 (2H, m), 1.82 (3H, s), 1.86 (2H, m), 2.58 (2H, m), 2.95 (2H, m), 3.46 (1H, m), 4.11 (4H, m); Mass Spectrum m/Z 188 (M+H)+.

Sources & evidence

ORD record
ord-906650c6cd6d4607bdc27dfe139ecf45
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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