N'-Hydroxybenzenecarboximidamide → 4-Benzyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)morpholine

HRID 1896171

反応式

HRID 1896171 の反応式
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]([OH:17])=O)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.O[N:61]=[C:62]([NH2:69])[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1>O>[CH2:2]([N:9]1[CH2:14][CH2:13][O:12][CH:11]([C:15]2[O:17][N:69]=[C:62]([C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)[N:61]=2)[CH2:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

7

反応物 5

HCID 69186N'-HydroxybenzenecarboximidamideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27763524-Benzylmorpholine-2-carboxylic acid hydrochloride2 回HCID 27960291-Hydroxybenzotriazole hydrate

生成物 1

HCID 469567114-Benzyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)morpholine収率 77%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a stirred solution of 4-benzyl-2-morpholinecarboxylic acid hydrochloride (intermediate 20, 1.5 g, 5.82 mmol) in N,N-dimethylformanide (10 ml) was added 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluroniumtetrafluoroborate (2.2 g, 6.98 mmol), 1-hydroxybenzotriazole hydrate (236 mg, 1.74 mmol) and N,N-diisopropylethylamine (5.1 ml, 29.1 mmol), and the reaction mixture was stirred at room temperature for 30 minutes. After the addition of N′-hydroxybenzamidine (792 mg, 5.82 mmol), the reaction mixture was stirred at room temperature for one hour, and then heated to 110° C. When the reaction was complete (checked by thin layer chromatography), excess reagent was decomposed by the addition of water and the aqueous layer was extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate, and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel, (eluent; 25% ethyl acetate in hexane) to afford 4-benzyl-2-(3-phenyl-1,2,4-oxadiazol-5-yl)morpholine (intermediate 21, 1.44 g, 77%) as a colorless oil.

後処理

  1. stirringthe reaction mixture was stirred at room temperature for one hour
  2. temperatureheated to 110° C
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe extract was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography on silica gel, (eluent; 25% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-41dca9b88d2249c28ca7fe902a4e6dde
出典データセット
uspto-grants-2013_08
特許番号
US08518939B2

関連ノート

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