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

HRID 480434Notes

Reaction equation

HRID 480434 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

At ice-bath temperature, lithium aluminium hydride (1.6 g, 42.16 mmol) was added in portions to a stirring mixture of (S)-2-benzylpiperazine-3,6-dione (3.0 g, 14.70 mmol) (comm. avail.) and tetrahydrofuran (80 ml). 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.MS (m/z)

Sources & evidence

ORD record
ord-d3a5f78ace2e4ee9aaaec1b5c7123f03
Source dataset
uspto-grants-2003_11
Patent number
US06649604B2

Reaction notes

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