Water → 1-benzyl-N-methylpiperidin-4-amine

HRID 448567Notes

Reaction equation

HRID 448567 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O[C:12](=O)[NH:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:15]1)(C)(C)C.O.[OH-].[Na+]>C1COCC1.C(OCC)(=O)C>[CH2:20]([N:17]1[CH2:18][CH2:19][CH:14]([NH:13][CH3:12])[CH2:15][CH2:16]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 44386181-Benzyl-4-(N-Boc-amino)piperidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 41361281-benzyl-N-methylpiperidin-4-amine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of LAH (0.5 g, 5 eq) in THF (10 mL), was added 7a and the mixture was refluxed for 72 h. After allowing the reaction mix to cool down to room temperature, 0.5 mL of water, 1 mL of 1 M sodium hydroxide and 1.5 mL of water were added slowly and sequentially. Ethyl acetate was added and the mixture was filtered. Removal of the solvent gave 0.36 g (66% on both steps) of 7b as an oil which was used without further purification on the next step.

Workup

  1. temperaturethe mixture was refluxed for 72 h
  2. additionmix
  3. filtrationthe mixture was filtered
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-3649616e70584b0e9fb7869b520b8a30
Source dataset
uspto-grants-2013_07
Patent number
US08481731B2

Reaction notes

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