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

HRID 1896124Notes

Reaction equation

HRID 1896124 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 1 N 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 1 N NaOH (aqueous)
  2. extractionThe product was extracted once with dichloromethane
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-92c6b9fe2fb84578bbc508ed2bad60a5
Source dataset
uspto-grants-2013_08
Patent number
US08518933B2

Reaction notes

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