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Triethylamine → 1-Benzyl-4-[N-(o-nitrobenzyl)-amino]-piperidine dihydrochloride

HRID 67065
Notes
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Reaction equation

HRID 67065 reaction equation
[ClH:1].Cl.[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([NH2:16])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N+:17]([C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O)([O-:19])=[O:18].C(N(CC)CC)C.[BH4-].[Na+]>CO>[ClH:1].[ClH:1].[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([NH:16][CH2:22][C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2[N+:17]([O-:19])=[O:18])[CH2:12][CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 111012-NitrobenzaldehydeHCID 4311764Sodium borohydrideHCID 125944831-Benzylpiperidin-4-amine dihydrochloride

Product 1

HCID 130510191-Benzyl-4-[N-(o-nitrobenzyl)-amino]-piperidine dihydrochlorideYield 73.1%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

In this reference example, 5.24 g of 1-benzyl-4-amino-piperidine dihydrochloride, 3.02 g of o-nitrobenzaldehyde, 2.02 g of triethylamine and 30 ml of methanol are mixed and stirred at room temperature for one hour. The resultant solution is cooled with ice and stirred. To the stirred solution, 1 g of sodium borohydride is added little by little over a period of one hour. Then, the mixture is brought back to room temperature and stirred at room temperature for 2 hours. The resultant solution is poured into 200 ml of ice water and extracted with ether. The organic layer is washed with water, dried and concentrated. The oily residue is dissolved in 20 ml of ethanol. The solution is mixed with 10 ml of a solution of 5.7 N hydrochloric acid in ethyl acetate. The white crystals deposited are separated by filtration, washed with 20 ml of ethyl acetate and dried to obtain 5.70 g of a crude product. The crude product is recrystallized from hot ethanol to obtain 2.90 g of the desired product.

Workup

  1. stirringstirred
  2. customis brought back to room temperature
  3. stirringstirred at room temperature for 2 hours
  4. extractionextracted with ether
  5. washThe organic layer is washed with water
  6. customdried
  7. concentrationconcentrated
  8. dissolutionThe oily residue is dissolved in 20 ml of ethanol
  9. additionThe solution is mixed with 10 ml of a solution of 5.7 N hydrochloric acid in ethyl acetate
  10. customThe white crystals deposited are separated by filtration
  11. washwashed with 20 ml of ethyl acetate
  12. customdried
  13. customto obtain 5.70 g of a crude product
  14. customThe crude product is recrystallized from hot ethanol

Sources & evidence

ORD record
ord-619d1ae7e2054bb8a316ed4a01e897db
Source dataset
uspto-grants-1982_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04344945

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes