Water → 1-Formyl-4-(2-bromo-4-methoxyphenyl)piperazine

HRID 1417808ノート

反応式

HRID 1417808 の反応式
[CH:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)=[O:2].C([O-])(=O)C.[Na+].[Br:22]Br.O>C(O)(=O)C>[CH:1]([N:3]1[CH2:4][CH2:5][N:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=2[Br:22])[CH2:7][CH2:8]1)=[O:2]

参加物

6

反応物 4

HCID 962Water2 回HCID 24408BromineHCID 517045Sodium AcetateHCID 232887711-Formyl-4-(4-methoxyphenyl)piperazine2 回

生成物 1

HCID 232888181-Formyl-4-(2-bromo-4-methoxyphenyl)piperazine

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

Sodium acetate (VI, 9.702 g, 0.1182 mol) is added to a mixture of 1-formyl-4-(4-methoxyphenyl)piperazine (VI, 5.17 g, 23.5 mmol) and acetic acid (102 ml). When the sodium acetate had completely dissolved, a solution of bromine (7.912 g, 49.5 mmol) in acetic acid (9.5 ml) is added over 14 min. After 35 min the mixture is poured into water poured into water and extracted exhaustively with dichloromethane. The combined organic extracts are backwashed with water, followed by saturated sodium bicarbonate, dried over sodium sulfate and concentrated. The residue is chromatographed on silica gel eluting first with ethyl acetate/dichloromethane (10/90) and then ethyl acetate/dichloromethane (20/80). The appropriate fractions are pooled and concentrated to give 1-formyl-4-(2-bromo-4-methoxyphenyl)piperazine (VII), NMR (CDCl3) 2.94, 3.55, 3.74, 3.78, 6.83, 6.97, 7.16 and 8.10 δ.

後処理

  1. extractionextracted exhaustively with dichloromethane
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel eluting first with ethyl acetate/dichloromethane (10/90)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-4ca8cc2a279842ea8bc7db6abedaa9ce
出典データセット
uspto-grants-1999_03
特許番号
US05877317

反応ノート

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