Aluminium lithium hydride → HCID 70202011, compound

HRID 342599Notes

Reaction equation

HRID 342599 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:14][CH2:15][C:16]([CH3:38])([CH3:37])[C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH2:32][C:33]([F:36])([F:35])[F:34])[CH2:21][CH2:20]1)=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1.O>[CH2:7]([O:14][CH2:15][C:16]([CH3:38])([CH3:37])[CH2:17][N:19]1[CH2:20][CH2:21][N:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[O:31][CH2:32][C:33]([F:34])([F:36])[F:35])[CH2:23][CH2:24]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 70202763HCID 70202763, compound

Product 1

HCID 70202011HCID 70202011, compoundYield 96.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of lithium aluminum hydride (0.49 g, 12.8 mmol) and THF (5 mL) was cooled to 0° C. and added to a solution of 3-benzyloxy-2,2-dimethyl-1-{4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}-1-propanone (2.8 g, 6.4 mol) in 12 mL of THF. The mixture was heated 2 hours at reflux, slowly diluted with water, filtered and concentrated. The residue was dissolved in water and the solution was extracted with methylene chloride (4×30 mL). The combined extracts were washed with water (1×25 mL), dried (MgSO4) and concentrated. The residue was purified by chromatography on silica gel eluting with hexanes/ethyl acetate (8:2) to give 3-benzyloxy-2,2-dimethyl-1-{4-[2-(2,2,2-trifluoroethoxy)phenyl]piperazin-1-yl}propane (2.6 g, 6.2 mol).

Workup

  1. temperatureThe mixture was heated 2 hours
  2. temperatureat reflux
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in water
  6. extractionthe solution was extracted with methylene chloride (4×30 mL)
  7. washThe combined extracts were washed with water (1×25 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe residue was purified by chromatography on silica gel eluting with hexanes/ethyl acetate (8:2)

Sources & evidence

ORD record
ord-e89266cc4ad440a9a12670b13c48b5eb
Source dataset
uspto-grants-1999_01
Patent number
US05859014

Reaction notes

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