Hydrazine → tert-Butyl 4-(aminooxy)piperidine-1-carboxylate

HRID 1895929Notes

Reaction equation

HRID 1895929 reaction equation
NN.O=C1C2C(=CC=CC=2)C(=O)[N:5]1[O:14][CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1>C(O)C>[NH2:5][O:14][CH:15]1[CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 21751544Tert-butyl 4-(1,3-dioxoisoindolin-2-yloxy)piperidine-1-carboxylate

Product 1

HCID 24729482tert-Butyl 4-(aminooxy)piperidine-1-carboxylateYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine solution (1.40 g, 29.0 mmol) was added to a solution of tert-butyl 4-(1,3-dioxoisoindolin-2-yloxy)piperidine-1-carboxylate (5.00 g, 14.5 mmol) in ethanol (50 ml) and stirred at room temperature for 30 minutes. The resulting solid was filtered off and the filtrate was concentrated in vacuo. The residue was triturated with diethyl ether (30 ml), and the resulting solid was filtered off again and concentrated in vacuo to give tert-butyl 4-(aminooxy)piperidine-1-carboxylate (2.75 g, 88%) as a white solid.

Workup

  1. filtrationThe resulting solid was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was triturated with diethyl ether (30 ml)
  4. filtrationthe resulting solid was filtered off again
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dd6393b58ca6440cba90dc0bf4b8bfdd
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

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