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1-(3-Chlorophenyl)ethanone → cis-1-[3-(3,5-Dimethyl-piperazin-1-yl)-phenyl]-ethanone

HRID 885853
ノート
印刷プレビュー

反応式

HRID 885853 の反応式
[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.Cl[C:38]1[CH:39]=[C:40]([C:44](=[O:46])[CH3:45])[CH:41]=[CH:42][CH:43]=1.[CH3:47][C@@H:48]1[CH2:53][NH:52][CH2:51][C@H:50]([CH3:54])[NH:49]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].COCCOC>[CH3:47][C@H:48]1[NH:49][C@@H:50]([CH3:54])[CH2:51][N:52]([C:38]2[CH:39]=[C:40]([C:44](=[O:46])[CH3:45])[CH:41]=[CH:42][CH:43]=2)[CH2:53]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 149331-(3-Chlorophenyl)ethanoneHCID 62657Potassium Phosphate, TribasicHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl2 回HCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

生成物 1

HCID 67049822cis-1-[3-(3,5-Dimethyl-piperazin-1-yl)-phenyl]-ethanone収率 15%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒2 回
HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
100 °C

実験手順

An oven-dried MW tube was charged with Pd2(dba)3 (592 mg, 0.65 mmol), K3PO4 (1.92 g, 9.06 mmol) and (2′-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethyl-amine (127 mg, 0.32 mmol). The tube was purged and backfilled with N2 and then 1-(3-chloro-phenyl)-ethanone (1 g, 6.47 mmol), (2R,6S)-2,6-dimethyl-piperazine (886 mg, 7.76 mmol) and DME (10 ml) were added. The mixture was heated in a MW apparatus for 4 h at 100° C. and then further Pd2(dba)3 (592 mg, 0.65 mmol) and (2′-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethyl-amine (127 mg, 0.32 mmol) were added. The reaction mixture was heated to 100° C. for additional 10 h and then the solid was filtered off over a Celite pad. The filtrate was diluted with AcOEt and extracted with 1 M HCl. The aqueous phase was brought to basic conditions with NH4OH and extracted with AcOEt. The organic phase was dried over Na2SO4 and evaporated in vacuo. The crude reaction mixture was purified by column chromatography (eluent: AcOEt/MeOH 8:2) to give 226 mg of 1-[3-((3R,5S)-3,5-dimethyl-piperazin-1-yl)-phenyl]-ethanone.

後処理

  1. customThe tube was purged
  2. temperatureThe reaction mixture was heated to 100° C. for additional 10 h
  3. filtrationthe solid was filtered off over a Celite pad
  4. additionThe filtrate was diluted with AcOEt
  5. extractionextracted with 1 M HCl
  6. extractionextracted with AcOEt
  7. dry with materialThe organic phase was dried over Na2SO4
  8. customevaporated in vacuo
  9. customThe crude reaction mixture
  10. customwas purified by column chromatography (eluent: AcOEt/MeOH 8:2)

出典と根拠

ORDレコード
ord-0c68304cf3754641a341323b02e2bcfd
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08242175B2

反応ノート

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