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

HRID 2181035

반응식

HRID 2181035 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d70075e51e554e93bf0665831b220bc7
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06890934B2

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