1,2-Dichloro-4-isothiocyanatobenzene → N-(3,4-Dichlorophenyl)-4-[(1-methylpiperidin-3-yl)methyl]piperazine-1-carbothioamide

HRID 603171ノート

反応式

HRID 603171 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH2:3]1.C[Si]([NH-])(C)C.[Na+].[Cl:21][C:22]1[CH:23]=[C:24]([N:29]=[C:30]=[S:31])[CH:25]=[CH:26][C:27]=1[Cl:28]>C(Cl)(Cl)Cl.C1COCC1>[Cl:21][C:22]1[CH:23]=[C:24]([NH:29][C:30]([N:12]2[CH2:13][CH2:14][N:9]([CH2:8][CH:4]3[CH2:5][CH2:6][CH2:7][N:2]([CH3:1])[CH2:3]3)[CH2:10][CH2:11]2)=[S:31])[CH:25]=[CH:26][C:27]=1[Cl:28]

参加物

6

反応物 3

HCID 230651,2-Dichloro-4-isothiocyanatobenzeneHCID 27369401-[(1-Methylpiperidin-3-yl)methyl]piperazineHCID 23692414Sodium trimethylsilylamide

生成物 1

HCID 57656911N-(3,4-Dichlorophenyl)-4-[(1-methylpiperidin-3-yl)methyl]piperazine-1-carbothioamide

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-[(1-methylpiperidin-3-yl)methyl]piperazine (400 mg) in chloroform (10 ml) was added a 2M solution of sodium(trimethylsilyl)amide in THF (2.2 ml). The resulting solution was stirred at room temperature for 10 minutes. 3,4-Dichlorophenylisothiocyanate (0.44 ml) was added and mixture stirred at room temperature for 1 hour. The reaction was quench with water (1 ml) then concentrated in vacuo before being separated between ethyl acetate (100 ml) and saturated sodium bicarbonate solution (100 ml). The ethyl acetate layer was separated, dried over magnesium sulphate, filtered then concentrated in vacuo onto silica gel (1.0 g). The resulting powder was purified by column chromatography on silica gel (50 g) using a gradient of 100% dichloromethane through to 10% methanolic ammonia in dichloromethane to give the title compound (726 mg).

後処理

  1. stirringmixture stirred at room temperature for 1 hour
  2. customThe reaction was quench with water (1 ml)
  3. concentrationthen concentrated in vacuo
  4. custombefore being separated between ethyl acetate (100 ml) and saturated sodium bicarbonate solution (100 ml)
  5. customThe ethyl acetate layer was separated
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationthen concentrated in vacuo onto silica gel (1.0 g)
  9. customThe resulting powder was purified by column chromatography on silica gel (50 g)

出典と根拠

ORDレコード
ord-d978f6ca656e4f4889cff30c9f95199b
出典データセット
uspto-grants-2011_03
特許番号
US07906645B2

反応ノート

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