4-Nitrobenzaldehyde → N-(4-nitrobenzyl)cyclohexanamine

HRID 1715339Notes

Reaction equation

HRID 1715339 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[N+:15]([C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1)([O-:17])=[O:16].[CH:26]1([NH2:32])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.[OH-].[Na+]>C(O)(=O)C.C(Cl)Cl>[CH:26]1([NH:32][CH2:22][C:21]2[CH:24]=[CH:25][C:18]([N+:15]([O-:17])=[O:16])=[CH:19][CH:20]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

7

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 7965CyclohexylamineHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 813995N-(4-nitrobenzyl)cyclohexanamine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

Sodium triacetoxyborohydride (11.0 mmol, 2.33 g) was added to a mixture of 4-nitro-benzaldehyde Compound 4a (10.0 mmol, 1.51 g), cyclohexylamine Compound 10a (10.5 mmol, 1.2 mL) and glacial acetic acid (5 drops) in CH2Cl2 (40 mL) and the resulting suspension was allowed to stir at room temperature for 12 hrs. An aliquot of the reaction mixture showed the formation of product (MS m/e 235, 100%). The reaction mixture was basified with 2N NaOH solution and was extracted with CH2Cl2. The organic layer was washed with brine, separated and dried over Na2SO4. The drying agent was filtered and the solvent was removed in vacuo to yield cyclohexyl-(4-nitro-benzyl)-amine Compound 14a (1.56 g, 67%) as a yellow oil, which was used in the next step without further purification.

Workup

  1. extractionwas extracted 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

Sources & evidence

ORD record
ord-ed872168bbed4a31bd30e21504453a63
Source dataset
uspto-grants-2010_09
Patent number
US07799824B2

Reaction notes

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