Sodium Sulfate → 1-Benzyl-4-(2-hydroxyethyl)piperidin-4-ol

HRID 2233606Notes

Reaction equation

HRID 2233606 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1([OH:18])[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH2:11]([N:8]1[CH2:7][CH2:6][C:5]([CH2:4][CH2:3][OH:2])([OH:18])[CH2:10][CH2:9]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 59296478(1-Benzyl-4-hydroxy-piperidin-4-yl)-acetic acid methyl ester

Product 1

HCID 28029691-Benzyl-4-(2-hydroxyethyl)piperidin-4-olYield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 24 (1.70 g, 6.07 mmol) in anhydrous THF (40 mL) at 0° C. was slowly added a solution of lithium aluminium hydride (1.0M in THF) (12.1 mL, 12.1 mmol). The solution was then stirred at 0° C. for 1 hr and allowed to return to room temperature to be stirred for an additional 2 hrs. The resulting solution was poured in a cold 10% solution of sodium sulphate (300 mL), extracted with diethyl ether (3×75 mL), washed with brine and finally dried over magnesium sulphate to give the crude compound 25 (1.32 g, 87%) which was used as such in the next step. 1H NMR (400 MHz, MeOD) δ: 1.65 (m, 4H), 1.72 (t, 2H, J=7.06 Hz), 2.45 (m, 2H), 2.62 (m, 2H), 3.56 (s, 2H), 3.76 (t, 2H, J=7.06 Hz), 7.31 (m, 5H).

Workup

  1. customto return to room temperature
  2. stirringto be stirred for an additional 2 hrs
  3. extractionextracted with diethyl ether (3×75 mL)
  4. washwashed with brine
  5. dry with materialfinally dried over magnesium sulphate

Sources & evidence

ORD record
ord-9ecb52a2b9ec48ca93c97a43f041b5f0
Source dataset
uspto-grants-2010_05
Patent number
US07709516B2

Reaction notes

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