4-Nitrobenzaldehyde → 1-(4-Nitrobenzyl)piperidine

HRID 1715333Notes

Reaction equation

HRID 1715333 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1)([O-:17])=[O:16].[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.[OH-].[Na+]>C(O)(=O)C.C(Cl)Cl>[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH2:22][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[CH:20][CH:19]=1)([O-:17])=[O:16]

Participants

7

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 8082PiperidineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 7835411-(4-Nitrobenzyl)piperidine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

NaB(OAc)3H (6.6 mmol, 1.4 g) was added to a mixture of 4-nitro-benzaldehyde Compound 4a (6.0 mmol, 0.9 g), piperidine Compound 5a (9.0 mmol, 0.9 mL) and glacial acetic acid (5 drops) in CH2Cl2 (50 mL) and the resulting suspension was stirred at r.t. overnight. The reaction mixture was made basic with a 2N NaOH solution and extracted with CH2Cl2. The organic layer was washed with brine, then separated and dried over Na2SO4. The drying agent was filtered and the solvent was removed in vacuo. The product was purified by flash column chromatography (10:1 EtOAc:MeOH) to yield 1-(4-nitro-benzyl)-piperidine Compound 5b as a yellow oil (0.89 g, 67% yield). MS m/e 221 (M+H, 100%).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with brine
  3. customseparated
  4. dry with materialdried over Na2SO4
  5. filtrationThe drying agent was filtered
  6. customthe solvent was removed in vacuo
  7. customThe product was purified by flash column chromatography (10:1 EtOAc:MeOH)

Sources & evidence

ORD record
ord-a1c73bc34a6e4a44b62632f09af7dac9
Source dataset
uspto-grants-2010_09
Patent number
US07799824B2

Reaction notes

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