Aluminium lithium hydride → [4-(4-Chlorophenyl)piperidin-4-yl]methanol

HRID 2104244Notes

Reaction equation

HRID 2104244 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:15](O)=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([CH2:15][OH:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 690497324-(4-Chloro-phenyl)-piperidine-4-carboxylic acid hydrochloride

Product 1

HCID 23136990[4-(4-Chlorophenyl)piperidin-4-yl]methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Took 3.0 g of 4-(4-chloro-phenyl)-piperidine-4-carboxylic acid hydrochloride (10.9 mmol, 1.00 equiv.) and 20 mL dry THF in a 250 mL round bottom flask fitted with a stir bar, reflux condenser, and N2 inlet. The resulting slurry was cooled in an ice water bath, followed by the addition of 825 mg LiAlH4 in several small portions. The ice bath was removed and the mixture allowed to stir overnight at room temperature under N2. The reaction was carefully quenched with a small amount of aqueous NaOH and allowed to stir for several hours. The solids were removed by vacuum filtration and discarded; the mother liquor was concentrated under vacuum and purified by normal phase HPLC (MeOH-DCM as the eluent). MS (ES) M+H expected=226.7, found=226.1

Workup

  1. temperaturereflux condenser, and N2 inlet
  2. temperatureThe resulting slurry was cooled in an ice water bath
  3. customThe ice bath was removed
  4. customThe reaction was carefully quenched with a small amount of aqueous NaOH
  5. stirringto stir for several hours
  6. customThe solids were removed by vacuum filtration
  7. concentrationthe mother liquor was concentrated under vacuum
  8. custompurified by normal phase HPLC (MeOH-DCM as the eluent)

Sources & evidence

ORD record
ord-a6046e7e6a7b4e44aa53ba7bc18650d5
Source dataset
uspto-grants-2009_08
Patent number
US07576218B2

Reaction notes

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