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

HRID 1601898Notes

Reaction equation

HRID 1601898 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 reaction mixture is stirred for 1 hour at RT and then heated for 1 hour at 40° C. It is cooled in an ice bath and 3 ml of water, 3 ml of 4 N NaOH solution and 12 ml of water are added successively. The mineral salts are filtered off and the filtrate is evaporated under vacuum. The residue is chromatographed on silica H using a gradient of a DCM/MeOH mixture (from 100/3; v/v to 100/10; v/v) as the eluent to give 11 g of the expected product.

Workup

  1. temperatureheated for 1 hour at 40° C
  2. temperatureIt is cooled in an ice bath
  3. filtrationThe mineral salts are filtered off
  4. customthe filtrate is evaporated under vacuum
  5. customThe residue is chromatographed on silica H

Sources & evidence

ORD record
ord-51d4befe1e4a4621b4b170c3554455f6
Source dataset
uspto-grants-1999_11
Patent number
US05977359

Reaction notes

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