Ethanolamine → tert-Butyl 4-(2-hydroxyethylamino)piperidine-1-carboxylate

HRID 2234187Notes

Reaction equation

HRID 2234187 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].O=[C:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1>[Pd].C(O)C.C(O)(=O)C>[OH:2][CH2:1][CH2:3][NH:4][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1

Participants

6

Reactant 2

HCID 700EthanolamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 23131007tert-Butyl 4-(2-hydroxyethylamino)piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A slurry of 10% palladium on charcoal (catalytic) in dry ethanol (3 mL) and acetic acid (5 drops) was added to a solution of ethanolamine (0.24 mL) and tert-butyl 4-oxopiperidine-1-carboxylate (0.80 g) in dry ethanol (10 mL) and hydrogenated at 2 bar for 26 hours. The solution was filtered through a glass fibre filter and the filtrate concentrated in vacuo to give the sub-titled compound (0.98 g) as a pale yellow oil.

Workup

  1. filtrationThe solution was filtered through a glass fibre
  2. filtrationfilter
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-924d2ea8f66e4a14821763bf5c6628a3
Source dataset
uspto-grants-2010_05
Patent number
US07709511B2

Reaction notes

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