Cyclo(-Gly-Phe) → (S)-2-Benzylpiperazine

HRID 566701Notes

Reaction equation

HRID 566701 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([C@H:14]1[C:19](=O)[NH:18][CH2:17][C:16](=O)[NH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCCC1>[CH2:7]([C@H:14]1[CH2:19][NH:18][CH2:17][CH2:16][NH:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 7076549Cyclo(-Gly-Phe)HCID 21226445Aluminium lithium hydride

Product 1

HCID 20760001(S)-2-Benzylpiperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (1.6 g, 42.16 mmol) was added in portions to a stirred mixture of (S)-2-benzylpiperazine-3,6-dione (3.0 g, 14.70 mmol) and tetrahydrofuran (80 ml) at 0° C. After 30 min at ice-bath temperature, the mixture was refluxed for 4 h with stirring. The reaction was quenched by the portionwise addition of sodium sulfate decahydrate and some methanol until hydrogen evolution ceased. It was filtered and the solids were washed several times with dichloromethane. The combined filtrates were evaporated to leave a white solid. MS (m/z): 177.1 (M+H)+; C11H16N2 requir. 176.3.

Workup

  1. temperaturethe mixture was refluxed for 4 h
  2. customThe reaction was quenched by the portionwise addition of sodium sulfate decahydrate
  3. filtrationIt was filtered
  4. washthe solids were washed several times with dichloromethane
  5. customThe combined filtrates were evaporated
  6. customto leave a white solid

Sources & evidence

ORD record
ord-651dea85a36543c19d67a363756ac87e
Source dataset
uspto-grants-2001_01
Patent number
US06174901B1

Reaction notes

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