Tetrahydrofuran → HCID 22004666, compound

HRID 324539Notes

Reaction equation

HRID 324539 reaction equation
C(O[C:4](=O)[CH2:5][CH2:6][CH:7]([N:9]1[CH2:14][CH2:13][CH2:12][CH:11]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10]1)C)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1C[O:32][CH2:31]C1>[NH4+].[Cl-]>[CH2:15]([CH:11]1[CH2:12][CH2:13][CH2:14][N:9]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:31][OH:32])[CH2:10]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 53997208HCID 53997208, compound

Product 1

HCID 22004666HCID 22004666, compound

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 4-[(3-benzyl)-1-piperidinyl]valeric acid ethyl ester (0.96 g, 3.31 mmol) in THF dry (20 mL) were added portionwise LiAlH4 (0.38 g, 9.95 mmol). The resulting mixture was stirred at 25° C. for 2 hrs then diluted with NH4Cl (sat. solution, 50 mL) and extracted with ethyl acetate (3×30 mL). The collected organic phases were washed with brine (50 mL), dried and concentrated in vacuum. The crude compound was purified by filtration on silica gel (260-400 mesh) using CH2Cl2/MeOH, 8/2 as solvent to give the title compound as an oil (0.70 g, 81). 1H-NMR (CDCl3): 0.8-1.0 (m, 1H); 1.3-1.45 (m, 2H); 1.45-1.75 (m, 9H); 1.8-2.0 (m, 2H); 2.25-2.4 (m, 2H); 2.4-2.6 (m, 2H); 2.78-2.93 (m, 2H); 3.607 (t, J=6.3, 2H); 7.136 (d, J=7.2, 2H); 7.186 (d, J=6.9, 1H); 7.264 (t, J=7.2, 2H).

Workup

  1. extractionextracted with ethyl acetate (3×30 mL)
  2. washThe collected organic phases were washed with brine (50 mL)
  3. customdried
  4. concentrationconcentrated in vacuum
  5. filtrationThe crude compound was purified by filtration on silica gel (260-400 mesh)

Sources & evidence

ORD record
ord-3080a60dd2e4430b8d2638c62b44702f
Source dataset
uspto-grants-2001_04
Patent number
US06218404B1

Reaction notes

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