Aluminium lithium hydride → 4-(4-Bromophenyl)-4-(4-chlorophenyl)-1-methylpiperidine

HRID 2361773Notes

Reaction equation

HRID 2361773 reaction equation
C(O[C:4]([N:6]1[CH2:11][CH2:10][C:9]([C:19]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][CH:20]=2)([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Br:25][C:22]1[CH:23]=[CH:24][C:19]([C:9]2([C:12]3[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=3)[CH2:10][CH2:11][N:6]([CH3:4])[CH2:7][CH2:8]2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59331961HCID 59331961, compound

Product 1

HCID 576913994-(4-Bromophenyl)-4-(4-chlorophenyl)-1-methylpiperidineYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere 4-(4-Bromo-phenyl)-4-(4-chloro-phenyl)-piperidine-1-carboxylic acid ethyl ester (0.28 g, 0.66 mmol) and lithium aluminum hydride (0.051 g) were suspended in tetrahydrofuran (5 ml) and stirred for 2 hours. The reaction mixture was quenched with addition of water, solvent removed under reduced pressure, the residue was partitioned between ethyl acetate and 2N NaOH. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated to afford the desired product (0.241 g, 99% yield). LC/MS: (PS-B3) Rt 3.78 [M+H]+ 363.95, 365.73.

Workup

  1. customThe reaction mixture was quenched with addition of water, solvent
  2. customremoved under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and 2N NaOH
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0a089ed6f6b24de7bd866d52391dfa76
Source dataset
uspto-grants-2014_04
Patent number
US08691806B2

Reaction notes

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