2-Chloro-6-nitrobenzaldehyde → (1-Benzyl-piperidin-4-yl)-(2-chloro-6-nitro-benzyl)-amine

HRID 239145Notes

Reaction equation

HRID 239145 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:3]=1[CH:4]=O.[NH2:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][CH2:15]1>C1(C)C=CC=CC=1>[CH2:20]([N:17]1[CH2:18][CH2:19][CH:14]([NH:13][CH2:4][C:3]2[C:6]([N+:10]([O-:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=2[Cl:1])[CH2:15][CH2:16]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 807012-Chloro-6-nitrobenzaldehydeHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 86686504(1-Benzyl-piperidin-4-yl)-(2-chloro-6-nitro-benzyl)-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

15 g 2-chloro-6-nitro-benzaldehyde and 4-amino-1-benzylpiperidine in 150 mL toluol were refluxed for 3 h. The toluol was removed and the residue was dissolved in 300 mL methanol. 6.6 g sodium borohydride was added and the reaction was refluxed over night. The solvent was removed, water and dichlormethane were added and the layers were separated. The organic layer was washed with water, dried and filtered to yield 29 g of the desired product.

Workup

  1. customThe toluol was removed
  2. dissolutionthe residue was dissolved in 300 mL methanol
  3. addition6.6 g sodium borohydride was added
  4. temperaturethe reaction was refluxed over night
  5. customThe solvent was removed
  6. additionwater and dichlormethane were added
  7. customthe layers were separated
  8. washThe organic layer was washed with water
  9. customdried
  10. filtrationfiltered

Sources & evidence

ORD record
ord-20a523238957474c8e3f76c2a6351590
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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