3-Chloro-4-methylaniline → 3-chloro-N-cyclohexylmethyl-4-methylaniline

HRID 2181035

Reaction equation

HRID 2181035 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[CH:10]1([CH:16]=O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.C([BH3-])#N.[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH:5][CH2:16][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 72553-Chloro-4-methylanilineHCID 16275CyclohexanecarboxaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 224851623-chloro-N-cyclohexylmethyl-4-methylanilineYield 85.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-chloro-4-methylaniline (7.08 g) in methanol (35 ml) were added cyclohexanecarbaldehyde (5.33 g) and sodium cyanoborohydride (3.78 g) under ice-cooling and the mixture was stirred at room temperature. After one hour, the reaction mixture was concentrated and water and saturated brine were added. The mixture was extracted 3 times with ethyl acetate. The organic layers were combined, washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate=15/1) to give 3-chloro-N-cyclohexylmethyl-4-methylaniline as a pale-yellow oil (9.64 g).

Workup

  1. temperaturecooling
  2. concentrationthe reaction mixture was concentrated
  3. additionwater and saturated brine were added
  4. extractionThe mixture was extracted 3 times with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate=15/1)

Sources & evidence

ORD record
ord-d70075e51e554e93bf0665831b220bc7
Source dataset
uspto-grants-2005_05
Patent number
US06890934B2

Linked notes

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