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Ammonium Chloride → 1-(Diphenylmethyl)-4-[(2-phenyl-4-methylfuran-5-yl)eth-1-yl]piperazine

HRID 1077845
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HRID 1077845 반응식
[C:1]1([C:7]2[O:8][C:9]([CH:13]=O)=[C:10]([CH3:12])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]1([CH:21]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH3:34][Mg]I.[Cl-].[NH4+].C(=O)(O)[O-].[Na+]>O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(Cl)Cl.C(OCC)C>[C:15]1([CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:28]2[CH2:29][CH2:30][N:31]([CH2:34][CH2:13][C:9]3[O:8][C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:11][C:10]=3[CH3:12])[CH2:32][CH2:33]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 5

HCID 25517Ammonium ChlorideHCID 70048BenzhydrylpiperazineHCID 516892Sodium BicarbonateHCID 194302672-Phenyl-4-methyl-5-formylfuranHCID 178418373HCID 178418373, 화합물

생성물 1

HCID 542165821-(Diphenylmethyl)-4-[(2-phenyl-4-methylfuran-5-yl)eth-1-yl]piperazine

시약·촉매·용매

4
HCID 11026Titanium isopropoxide촉매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매

실험 절차

A solution of 2-phenyl-4-methyl-5-formylfuran (1.1 g), diphenylmethylpiperazine (1.5 g), and titanium(IV)isopropoxide (1.76 g) was stirred for 11/4 hours. Diethyl ether (20 ml) was added, and the resultant solution was stirred for 30 minutes. Methyl magnesium iodide (6 ml of 3M in ether) was then added dropwise, and the mixture stirred at room temperature for 1 hour. Ammonium chloride (20 ml of a saturated solution in water) was then added, followed by 300 ml of methylene chloride, and the mixture made basic with a solution of sodium bicarbonate. The residue was partitioned between methylene chloride/water, the organic layer separated, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was flash-chromatographed on silica gel, eluting with 15% ethyl acetate in heptane with a trace of ammonia, to yield 0.51 g of 1-(diphenylmethyl)-4-[(2-phenyl-4-methylfuran-5-yl)eth-1-yl]piperazine. Treatment with anhydrous hydrochloric acid in ethanol converted the base to its dihydrochloride salt, m.p. 205°-8° C.

후처리

  1. customThe residue was partitioned between methylene chloride/water
  2. customthe organic layer separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was flash-chromatographed on silica gel
  7. washeluting with 15% ethyl acetate in heptane with a trace of ammonia

출처 및 근거

ORD 기록
ord-daa25151622044e381d6df788a9c3576
출처 데이터셋
uspto-grants-1996_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05545645

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