Chloroform → N-(4-tertiary-butylbenzyl)-N-methyl-3-phenoxybenzylamine

HRID 369375

반응식

HRID 369375 반응식
[C:1]([C:5]1[CH:13]=[CH:12][C:8]([CH2:9]CN)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[O:20]([C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30]Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(Cl)(Cl)Cl.[CH3:39][N:40](C)C=O>O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:40]([CH2:30][C:29]2[CH:32]=[CH:33][CH:34]=[C:27]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:28]=2)[CH3:39])=[CH:12][CH:13]=1)([CH3:2])([CH3:3])[CH3:4]

참가 물질

7

반응물 5

HCID 6212ChloroformHCID 6228Dimethylformamide2회HCID 10340Sodium CarbonateHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 27356892-(4-Tert-butylphenyl)ethan-1-amine

생성물 1

HCID 23286207N-(4-tertiary-butylbenzyl)-N-methyl-3-phenoxybenzylamine수율 87.8%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Following the process to be described below, Compound 1 was prepared. Namely, 10.16 g of m-phenoxytoluene, 9.82 g of N-bromosuccinimide and 0.15 g of benzoyl peroxide were weighed and added to 90 ml of carbon tetrachloride as a solvent. The resulting mixture was heated under reflux for 3 hours to conduct a reaction. The reaction mixture was allowed to cool down, the insoluble matter was filtered off, and the filtrate was then concentrated. The concentrate was purified by chromatography on a silica gel column (eluent: chloroform), whereby 10.9 g of 3-phenoxybenzyl bromide were obtained. In 20 ml of N,N-dimethylformamide, 2.79 g of N-(4-tert-butylbenzyl)methylamine and 1.67 g of sodium carbonate were mixed, to which a solution of 3.77 g of 3-phenoxybenzyl bromide in 25 ml of N,N-dimethylformamide was added dropwise under ice cooling. The temperature of the reaction mixture was allowed to rise to room temperature, at which a reaction was allowed to proceed for 12 hours. Chloroform and water were added to the reaction mixture to conduct liquid-liquid extraction. An organic layer was collected and then washed with water and a saturated aqueous solution of sodium chloride. The resulting solution was dried over anhydrous sodium sulfate and was then concentrated. The concentrate was purified by chromatography on a silica gel column (eluent:hexane:chloroform:ethyl acetate=9:1:0→0:10:0→0:0:100). Relevant fractions were concentrated, whereby 4.49 g of N-(4-tertiary-butylbenzyl)-N-methyl-3-phenoxybenzylamine (Compound 1) were obtained (yield: 87.8%). The following is its NMR data (CDCl3 δ ppm): 1.28(9H,s), 2.18(3H,s), 3.476(2H,s), 3.483(2H,s), 6.86-7.35(13H,m).

후처리

  1. additionwas added dropwise under ice cooling
  2. customto rise to room temperature, at which
  3. extractionliquid-liquid extraction
  4. customAn organic layer was collected
  5. washwashed with water
  6. dry with materialThe resulting solution was dried over anhydrous sodium sulfate
  7. concentrationwas then concentrated
  8. customThe concentrate was purified by chromatography on a silica gel column (eluent:hexane:chloroform:ethyl acetate=9:1:0→0:10:0→0:0:100)
  9. concentrationRelevant fractions were concentrated

출처 및 근거

ORD 기록
ord-c98210b707314d7a8dded572e9cca4cc
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06136863

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