2-Iodotoluene → N,N-Dimethyl-3-phenyl-3-(o-tolyloxy)propan-1-amine

HRID 1724098노트

반응식

HRID 1724098 반응식
[CH3:1][N:2]([CH2:4][CH2:5][CH:6]([OH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:3].I[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21].C(=O)([O-])[O-].[Cs+].[Cs+]>C(OC)(C)(C)C>[CH3:1][N:2]([CH2:4][CH2:5][CH:6]([O:13][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:3]

참가 물질

5

반응물 3

HCID 51282-IodotolueneHCID 10796Cesium carbonateHCID 1106653-(Dimethylamino)-1-phenylpropan-1-ol

생성물 1

HCID 12807420N,N-Dimethyl-3-phenyl-3-(o-tolyloxy)propan-1-amine수율 89.1%

시약·촉매·용매 1

HCID 15413tert-Butyl methyl ether용매

반응 조건

온도
130 °C

실험 절차

A mixture of N,N-dimethyl-3-hydroxy-3-phenylpropylamine (0.9 g, 5 mmol), 2-iodotoluene (1.31 g, 6 mmol), cuprous iodide (0.2 g) and cesium carbonate (1.8 g, 5.5 mmol) was stirred under nitrogen at 130° C. until the reaction was complete as determined by 1H NMR. The reaction mixture was cooled to room temperature, diluted with methyl t-butyl ether (10 mL), filtered, and rinsed with more methyl t-butyl ether. The filtrate was extracted with diluted hydrochloric acid solution and the aqueous layer was washed with more methyl t-butyl ether. The aqueous was adjusted to pH>10 by the addition of sodium hydroxide solution, then extracted with methyl t-butyl ether twice. The combined extracts were washed with water and then evaporated to dryness to give 1.2 g of N,N-dimethyl-3-(2-methylphenoxy)-3-phenylpropylamine as a light yellow oil. 1H NMR (CDCl3) δ 7.45-7.2 (m, 5H), 7.12 (d, J=6.8 Hz, 1H), 7.0 (dd, J=8.0, 7.6 Hz, 1H), 6.78 (dd, J=8.4, 6.8 Hz, 1H), 6.63 (d, J=8.1 Hz, 1H), 5.24 (dd, J=8.1, 4.8 Hz, 1H), 2.46 (t, J=7.3 Hz, 2H), 2.33 (s, 3H), 2.24 (s, 6H), 2.3-2.1 (m, 1H), 2.05-1.9 (m, 1H).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. washrinsed with more methyl t-butyl ether
  4. extractionThe filtrate was extracted with diluted hydrochloric acid solution
  5. washthe aqueous layer was washed with more methyl t-butyl ether
  6. additionThe aqueous was adjusted to pH>10 by the addition of sodium hydroxide solution
  7. extractionextracted with methyl t-butyl ether twice
  8. washThe combined extracts were washed with water
  9. customevaporated to dryness

출처 및 근거

ORD 기록
ord-70ecd5915f97497d92575d41ef8af620
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07485754B2

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