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

HRID 1077845

反応式

HRID 1077845 の反応式
[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

参加物

10

反応物 5

HCID 25517Ammonium ChlorideHCID 70048BenzhydrylpiperazineHCID 516892Sodium BicarbonateHCID 194302672-Phenyl-4-methyl-5-formylfuranHCID 178418373HCID 178418373、化合物

生成物 1

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

試薬・触媒・溶媒 4

HCID 11026Titanium isopropoxide触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-daa25151622044e381d6df788a9c3576
出典データセット
uspto-grants-1996_08
特許番号
US05545645

関連ノート

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