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Potassium Carbonate → [3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]-cyclohexylmethyl-amine

HRID 1643220
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HRID 1643220 반응식
[CH2:1]([N:5]1[C:9]([CH2:10]O)=[C:8]([C:12]2[CH:17]=[CH:16][C:15](OC)=[CH:14][CH:13]=2)[N:7]=[C:6]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:2][CH2:3][CH3:4].S(Cl)(Cl)=O.[CH:30]1([CH2:36][NH2:37])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.[C:38](=[O:41])([O-])[O-].[K+].[K+]>ClCCl.C(#N)C.C(OCC)(=O)C>[CH2:1]([N:5]1[C:9]([CH2:10][NH:37][CH2:36][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([O:41][CH3:38])=[CH:14][CH:13]=2)[N:7]=[C:6]1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:2][CH2:3][CH3:4]
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참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 76688CyclohexanemethylamineHCID 588180923-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethanol

생성물 1

HCID 58818024[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]-cyclohexylmethyl-amine

시약·촉매·용매 3

HCID 6342
Acetonitrile
용매
HCID 6344Dichloromethane용매
HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

4-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethanol (6.72 g, 20 mmol) is dissolved in 30 ml dichloromethane and cooled to 0° C., to the solution is added 5 equivalent of thionyl chloride. The resulting solution is stirred at room temperature for 2 h, the solvent and excess of thionyl chloride is evaporated. 20 ml of toluene is added to the residue and evaporated again to remove the remained thionyl chloride. The residual crude product is dissolved in 30 ml of anhydrous acetonitrile and added to an ice-cooled solution of cyclohexanemethyl amine (2.0 eq.) in 20 ml of acetonitrile containing, 2 equivalent of potassium carbonate. The resulting mixture is stirred at room temperature for 4 h, then diluted with 200 ml of ethyl acetate, washed with water and brine, dried and concentrated, the residue is purified through silica gel chromatography (hexanes/ethyl acetate, from 2:1 to 1:1) to give 11.26 g of 4-({[3-Butyl-5-(4-methoxy-phenyl)-2-phenyl-3H-imidazol-4-ylmethyl]-cyclohexylmethyl-amine. 1H NMR (400 MHz, CDCl3) δ 7.64˜7.60 (4H, m), 7.47˜7.40 (3H, m), 6.94 (2H, d, J=8.8 Hz), 4.11 (2H, m), 3.87 (2H, s), 3.84 (3H,s), 2.52 (H, d, J=6.4 Hz), 0.91˜1.77 (15H, m), 0.84 (3H, t, J=7.2 Hz); MS (+VE) m/z 432 (M+1).

후처리

  1. customthe solvent and excess of thionyl chloride is evaporated
  2. addition20 ml of toluene is added to the residue
  3. customevaporated again
  4. customto remove the remained thionyl chloride
  5. dissolutionThe residual crude product is dissolved in 30 ml of anhydrous acetonitrile
  6. additionadded to an ice-
  7. stirringThe resulting mixture is stirred at room temperature for 4 h
  8. washwashed with water and brine
  9. customdried
  10. concentrationconcentrated
  11. customthe residue is purified through silica gel chromatography (hexanes/ethyl acetate, from 2:1 to 1:1)

출처 및 근거

ORD 기록
ord-0c2d20128dd24cefb7cf6b011f951719
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08119665B2

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