Aluminium lithium hydride → 2-(Benzyloxymethyl)piperazine

HRID 1972402Notes

Reaction equation

HRID 1972402 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][CH2:15][CH:16]1[NH:21][C:20](=O)[CH2:19][NH:18][C:17]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([O:14][CH2:15][CH:16]1[CH2:17][NH:18][CH2:19][CH2:20][NH:21]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 665824363-(Benzyloxymethyl)piperazine-2,5-dione

Product 1

HCID 222773712-(Benzyloxymethyl)piperazineYield 76.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 250 ml, round-bottomed flask was charged with lithium aluminum hydride (1.871 g, 49.3 mmol) and THF (75 mL). After cooling to 0° C., 3-(benzyloxymethyl)piperazine-2,5-dione (3.85 g, 16.44 mmol) was slowly added. The mixture was warmed to room temperature and then heated at reflux for 1 h. After this time, the mixture was cooled to 0° C. and the reaction was quenched with sodium sulfate decahydrate (20 g) and stirred vigorously for 1 h. The mixture was filtered, and the filtrate was concentrated to give 2-(benzyloxymethyl)piperazine (2.60 g) as a yellow oil. This material was taken to the next step without purification.

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. temperatureheated
  3. temperatureat reflux for 1 h
  4. temperatureAfter this time, the mixture was cooled to 0° C.
  5. customthe reaction was quenched with sodium sulfate decahydrate (20 g)
  6. filtrationThe mixture was filtered
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-51ffdcd905ca419eb06362162b19d98e
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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