Water → 3-[(Dibenzylamino)methyl]cyclohexanamine

HRID 1269762Notes

Reaction equation

HRID 1269762 reaction equation
Cl.[NH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([C:9]([N:11]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=O)[CH2:4]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:12]([N:11]([CH2:9][CH:5]1[CH2:6][CH2:7][CH2:8][CH:3]([NH2:2])[CH2:4]1)[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 229334063-amino-N,N-dibenzylcyclohexane-carboxamide monohydrochloride

Product 1

HCID 184471283-[(Dibenzylamino)methyl]cyclohexanamineYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-amino-N,N-dibenzylcyclohexane-carboxamide monohydrochloride (0.848 g) in tetrahydrofuran (5 ml) was added dropwise to a suspension of lithium aluminum hydride (0.337 g, 8.89 mmol) in tetrahydrofuran (5 ml), and the resulting mixture was stirred with heating under reflux for 3 hours. The resulting solution was cooled on an ice bath, followed by adding dropwise thereto water (0.33 ml), a 2N-aqueous sodium hydroxide solution (0.66 ml) and water (1.0 ml) in that order. Thereafter, the insoluble material was removed by filtration using Celite. The solvent was distilled off from the filtrate under reduced pressure, followed by replacement with ethanol (once) and toluene (twice). Then, the residue was dried under reduced pressure to obtain 3-[(dibenzylamino)methyl]cyclohexanamine (0.550 g, 99%).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 3 hours
  3. temperatureThe resulting solution was cooled on an ice bath
  4. additionby adding dropwise
  5. customThereafter, the insoluble material was removed by filtration
  6. distillationThe solvent was distilled off from the filtrate under reduced pressure
  7. customThen, the residue was dried under reduced pressure

Sources & evidence

ORD record
ord-e65a446565b9440e9835a65bd04a2d18
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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