Water → 1-Benzyl-4-phenylpiperidine-4-methylamine

HRID 1597263Notes

Reaction equation

HRID 1597263 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][CH2:18][C:17]([C:26]#[N:27])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[NH2:27][CH2:26][C:17]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:18][CH2:19][N:14]([CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:15][CH2:16]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 1914081-Benzyl-4-cyano-4-phenylpiperidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 8042381-Benzyl-4-phenylpiperidine-4-methylamineYield 54.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 2.8 g of lithium aluminum hydride in 50 ml of THF is cooled to 0° C. and a solution of 20 g of 1-benzyl-4-cyano-4-phenylpiperidine in 50 ml of THF is added dropwise. The mixture is kept stirring for 1 hour at RT and then heated at 40° C. for 1 hour. The reaction mixture is cooled on an ice bath, and 3 ml of water, 3 ml of a 4N solution of NaOH and 12 ml of water are added successively. The inorganic salts are filtered and the filtrate evaporated under vacuum. The residue is chromatographed on silica H, eluting with the gradient of the DCM/MeOH mixture from (100/3; v/v) to (100/10; v/v). 11 g of the expected product are obtained.

Workup

  1. temperatureheated at 40° C. for 1 hour
  2. temperatureThe reaction mixture is cooled on an ice bath
  3. filtrationThe inorganic salts are filtered
  4. customthe filtrate evaporated under vacuum
  5. customThe residue is chromatographed on silica H
  6. washeluting with the gradient of the DCM/MeOH mixture from (100/3; v/v) to (100/10; v/v)

Sources & evidence

ORD record
ord-178d0cad4cc04375a2a0ab5afd5a7f55
Source dataset
uspto-grants-2001_09
Patent number
US06294537B1

Reaction notes

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