Water → (1-Benzyl-4-piperidyl)methanamine

HRID 1172279Notes

Reaction equation

HRID 1172279 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]([C:20]#[N:21])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>CCOCC>[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][NH2:21])[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 7933831-Benzylpiperidine-4-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 1514444(1-Benzyl-4-piperidyl)methanamineYield 114.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A suspension of LiAlH4 (4.84 g, 0.128 mol) in dry Et2O (40 ml) under argon atmosphere at 0° C. was dropwise added a solution of 1-benzyl-4-cyano-piperidine (18.3 g, 91.5 mmol) in dry Et2O (80 ml) and stirred to room temperature for 24 h. The reaction mixture was treated carefully with H2O (10 ml), 10% aqueous NaOH (10 ml) and H2O (30 ml) to give a mineral precipitate. The precipitate was filtered through a pad of kiselguhr, washed with Et2O and the filtrate evaporated in vacuo to leave the product as an oil (21.4 g, 82.3%).

Workup

  1. customto give a mineral precipitate
  2. filtrationThe precipitate was filtered through a pad of kiselguhr
  3. washwashed with Et2O
  4. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-6d527905610546759a3a40f18e55318e
Source dataset
uspto-grants-2010_11
Patent number
US07834010B2

Reaction notes

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