4-Methylmorpholine → (4-Bromo-2-chlorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone

HRID 2411250ノート

反応式

HRID 2411250 の反応式
Cl.[CH3:2][C:3]1[C:4]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[N:5][CH:6]=[C:7]([CH3:9])[CH:8]=1.[Br:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[C:19]([Cl:26])[CH:18]=1.CN1CCOCC1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>C(Cl)(Cl)Cl.CO.O>[Br:16][C:17]1[CH:25]=[CH:24][C:20]([C:21]([N:13]2[CH2:12][CH2:11][N:10]([C:4]3[C:3]([CH3:2])=[CH:8][C:7]([CH3:9])=[CH:6][N:5]=3)[CH2:15][CH2:14]2)=[O:22])=[C:19]([Cl:26])[CH:18]=1

参加物

8

反応物 4

HCID 79724-MethylmorpholineHCID 1088294-Bromo-2-chlorobenzoic acidHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 673813791-(3,5-Dimethylpyridin-2-yl)piperazine hydrochloride

生成物 1

HCID 58484833(4-Bromo-2-chlorophenyl)[4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl]methanone収率 99.1%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 6212Chloroform溶媒

実験手順

A mixture of 1-(3,5-dimethylpyridin-2-yl)piperazine hydrochloride (956 mg) described in Preparation Example 80, 4-bromo-2-chlorobenzoic acid (1 g) and N-methylmorpholine (465 μL) was dissolved in a solution of chloroform (6 mL) and methanol (6 mL), 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMT-MM) (1.7 g) was added, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (1.7 g).

後処理

  1. additionwas added
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with saturated brine
  4. customthe solvent was evaporated
  5. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

出典と根拠

ORDレコード
ord-c8feae5267a24c0995432593364111d6
出典データセット
uspto-grants-2014_08
特許番号
US08816079B2

反応ノート

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