2-Chloro-N,N-dimethylethylamine → Dimethyl[2-(2-phenylchroman-6-yloxy)ethyl]amine

HRID 31167

반응식

HRID 31167 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][N:8]([CH3:12])[CH2:9][CH2:10]Cl.[C:13]1([CH:19]2[CH2:28][CH2:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([OH:29])[CH:25]=3)[O:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OCC)(=O)C.C(#N)C>[CH3:7][N:8]([CH3:12])[CH2:9][CH2:10][O:29][C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[O:20][CH:19]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:28][CH2:27]2

참가 물질

6

반응물 3

HCID 79012-Chloro-N,N-dimethylethylamineHCID 10796Cesium carbonateHCID 212875382-Phenylchroman-6-ol

생성물 1

HCID 17978584Dimethyl[2-(2-phenylchroman-6-yloxy)ethyl]amine

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

Cesium carbonate (230 mg) and an excess of 2-(dimethylamino)ethyl chloride in ethyl acetate were added into a solution of 2-phenylchroman-6-ol (150 mg) in acetonitrile (5 ml). The reaction mixture was refluxed for 30 minutes. After removing the solvents, the residue was taken up in water and extracted with ethyl acetate. The combined organic layers were washed with water and then with saturated NaCl-solution and dried with Na2SO4. The dimethyl[2-(2-phenylchroman-6-yloxy)-ethyl]amine was crystallised from heptane. 1H NMR (400 MHz, d6-DMSO) δ: 7.43-7.30 (m, 5H), 6.75-6.67 (m, 3H), 5.03 (dd, 1H, J 10.0, 2.2 Hz), 3.95 (t, 2H, J 5.9 Hz), 2.94 (ddd, 1H, J −16.7, 10.9, 5.8 Hz), 2.69 (ddd, 1H, J −16.7, 5.2, 3.3 Hz), 2.58 (t, 2H, J 5.9 Hz), 2.13 (m, 1H), 1.96 (m, 1H).

후처리

  1. temperatureThe reaction mixture was refluxed for 30 minutes
  2. customAfter removing the solvents
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with water
  5. dry with materialwith saturated NaCl-solution and dried with Na2SO4
  6. customThe dimethyl[2-(2-phenylchroman-6-yloxy)-ethyl]amine was crystallised from heptane

출처 및 근거

ORD 기록
ord-114c319582744b84bd6f0d497c324daf
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425568B2

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