HCID 12833276, compound → 2,4-Dimethyl-5-(1-piperidinyl)benzenamine

HRID 848037Notes

Reaction equation

HRID 848037 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:9]=[C:10]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]2=O)[C:11]([CH3:15])=[CH:12][C:13]=1[CH3:14]>O1CCCC1>[NH2:7][C:8]1[CH:9]=[C:10]([N:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[C:11]([CH3:15])=[CH:12][C:13]=1[CH3:14]

Participants

4

Reactant 2

HCID 12833276HCID 12833276, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 130623362,4-Dimethyl-5-(1-piperidinyl)benzenamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.2 g of lithium aluminium hydride are introduced into 200 ml of absolute tetrahydrofuran. 26 g (0.12 mol) of 1-(3'-amino-4',6'-dimethylphenyl)-piperidin-2-one are added in portions, with stirring. The mixture is then refluxed for 1 hour. Excess LiAlH4 is destroyed with ethyl acetate. 2 N Hcl is added to the mixture until the pH is 4-5, ether is added and the mixture is extracted twice with 2 N KOH solution. The organic phase is washed with water and saturated NaCl solution, dried with MgSO4, clarified with active charcoal and evaporated. The residue is distilled in a bulb tube. This gives 18.2 g (73%) of a yellow oil (boiling point 140°/0.001 mm Hg).

Workup

  1. temperatureThe mixture is then refluxed for 1 hour
  2. customExcess LiAlH4 is destroyed with ethyl acetate
  3. addition2 N Hcl is added to the mixture until the pH is 4-5, ether
  4. additionis added
  5. extractionthe mixture is extracted twice with 2 N KOH solution
  6. washThe organic phase is washed with water and saturated NaCl solution
  7. dry with materialdried with MgSO4
  8. customevaporated
  9. distillationThe residue is distilled in a bulb tube

Sources & evidence

ORD record
ord-6523d336c32147acb589d32f1f061f72
Source dataset
uspto-grants-1981_10
Patent number
US04294606

Reaction notes

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