Ethyl 4-benzyl-3-oxopiperazine-2-carboxylate → (4-benzylpiperazin-2-yl)methanol

HRID 80507Notes

Reaction equation

HRID 80507 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([C:14](OCC)=[O:15])[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([CH2:14][OH:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 15645951Ethyl 4-benzyl-3-oxopiperazine-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2756656(4-benzylpiperazin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Example 45B (6 g, 22.87 mmol) in tetrahydrofuran (45.7 mL) was added to lithium aluminum hydride in tetrahydrofuran (30.9 mL, 61.8 mmol) dropwise with an addition funnel under nitrogen over 30 minutes. The reaction mixture was stirred at room temperature for 1 hour and then carefully quenched with water and 1N NaOH(aqueous). The product was extracted once with dichloromethane, dried over Na2SO4 and concentrated to afford the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.37-7.17 (m, 5H), 4.48 (t, J=5.4, 1H), 3.60 (t, J=6.5, 1H), 3.42 (q, J=13.1, 2H), 3.27-3.15 (m, 2H), 2.80 (dt, J=2.7, 11.4, 1H), 2.73-2.55 (m, 4H), 1.92 (td, J=3.0, 10.8, 1H), 1.81-1.72 (m, 1H), 1.60 (t, J=10.1, 1H); MS (ESI+) m/z 206.9 (M+H)+.

Workup

  1. customcarefully quenched with water and 1N NaOH(aqueous)
  2. extractionThe product was extracted once with dichloromethane
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-775c9076fd6842eeae69ef0aad32d641
Source dataset
uspto-grants-2014_09
Patent number
US08846663B2

Reaction notes

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