Ethyl Acetate → (1-Benzylpiperidin-4-yl)methanol

HRID 1291190Notes

Reaction equation

HRID 1291190 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]([C:20](OCC)=[O:21])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(OCC)(=O)C.[OH-].[Na+]>C1COCC1.O>[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][OH:21])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 90423Ethyl 1-benzylpiperidine-4-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 736802(1-Benzylpiperidin-4-yl)methanolYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.42 g (0.0375 mol) of lithium aluminium hydride were suspended in 20 ml of THF. 1.548 g (0.00623 mol) of ethyl 1-benzylpiperidine-4-carboxylate were slowly added dropwise at 0°. The mixture was heated to 70° and boiled at reflux for 16 hrs. The reaction mixture was treated with 70 ml of ethyl acetate, 6.5 ml of water and 1.5 ml of 2N aqueous NaOH. The mixture was stirred for 1 hr., the precipitate was filtered off and the filtrate was concentrated. The residue was chromatographed on silica gel with methanol/dichloromethane (1:9) as the eluent. 1.16 g (91%) of 1-benzyl-4-hydroxymethylpiperidine were obtained.

Workup

  1. temperatureThe mixture was heated to 70°
  2. temperatureat reflux for 16 hrs
  3. filtration, the precipitate was filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe residue was chromatographed on silica gel with methanol/dichloromethane (1:9) as the eluent

Sources & evidence

ORD record
ord-185d6310657e4de0b676b51e57848580
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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