Water → 4-Phenylpiperidine-4-methanol

HRID 406512

Reaction equation

HRID 406512 reaction equation
[C:1]1([C:7]2([C:13](O)=[O:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[C:1]1([C:7]2([CH2:13][OH:14])[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 192594-Phenylpiperidine-4-carboxylic acid, compound with toluene-p-sulphonic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 778964-Phenylpiperidine-4-methanolYield 50.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-phenyl-piperidine-4-carboxylic acid (0.168 g, 0.819 mmol) in THF (2 mL) was added dropwise to a 0° C. solution of lithium aluminum hydride (1.0N in THF, 1.63 mL, 1.64 mmol). The reaction was stirred at room temperature for about 16 h. Water (1 mL) was added to the reaction mixture, followed by 2 N NaOH (1 mL). The solution was stirred for about 1 h then filtered. The filtrate was extracted with DCM (25 mL) and the organic layer was separated. The aqueous layer was further extracted with dichloromethane (2×25 mL). The combined organic extracts were dried over magnesium sulfate, filtered and evaporated under reduced pressure to give (4-phenyl-piperidin-4-yl)-methanol (0.078 g, 0.41 mmol) as brown oil, which was used in subsequent reactions without further purification. RP-HPLC (Table 1, Method b) Rt 1.24 min; m/z: (M+H)+ 192.

Workup

  1. stirringThe solution was stirred for about 1 h
  2. filtrationthen filtered
  3. extractionThe filtrate was extracted with DCM (25 mL)
  4. customthe organic layer was separated
  5. extractionThe aqueous layer was further extracted with dichloromethane (2×25 mL)
  6. dry with materialThe combined organic extracts were dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ce1d76a895844dfb981052d595b55813
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Linked notes

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