HCID 15445561, compound → 139004-92-5

HRID 2082344Notes

Reaction equation

HRID 2082344 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([NH:14][C:15]([C@@H:17]1[CH2:22][CH2:21][CH2:20][CH2:19][NH:18]1)=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([N:14]1[CH2:15][CH2:17][CH2:22][CH2:21][C@H:20]1[CH2:19][NH2:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 15445561HCID 15445561, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15667836139004-92-5Yield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a solution of 230 mL (0.23 mmol) of 1M lithium aluminum hydride in THF was added over 20 min a solution of (S)-N-benzylpiperidine-2-carboxamide in 150 mL of THF. The mixture was refluxed for 5 h, diluted with 500 ml of THF, cooled to -78° C. and quenched with a solution of 48 mL 1N aqueous sodium hydroxide in 200 mL THF. The resulting slurry was filtered through a Celite® pad and concentrated at reduced pressure to yield (S)-N-benzyl-2-aminomethylpiperidine (10.9 g, 89%).

Workup

  1. temperatureThe mixture was refluxed for 5 h
  2. customquenched with a solution of 48 mL 1N aqueous sodium hydroxide in 200 mL THF
  3. filtrationThe resulting slurry was filtered through a Celite® pad
  4. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-6c240e21cfbc43ad84c1742f8ba70bbc
Source dataset
uspto-grants-1993_02
Patent number
US05189046

Reaction notes

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