N-(2-Methoxyphenyl)piperazine hydrochloride → 1-(2-Methoxyphenyl)piperazine

HRID 277757

反応式

HRID 277757 の反応式
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1>O>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1

参加物

3

反応物 1

HCID 9899402N-(2-Methoxyphenyl)piperazine hydrochloride

生成物 1

HCID 13461-(2-Methoxyphenyl)piperazine収率 96%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a solution of 25.00 g (0.1093 mol) of 1-(2′-methoxyphenyl)piperazine hydrochloride in 42 mL of water was added 14.5 mL (0.109 mol) of concentrated (29.4%) NH4OH (aq) (pH=9). The mixture was extracted twice with 250 mL of 1:1 (v/v) of THF:toluene. The organic extracts were combined, dried over MgSO4, gravity filtered and concentrated to afford 20.17 g (96.00%) of 1-(2′-methoxyphenyl)piperazine as a pale green oil: 1H NMR (d6-DMSO): d 6.90-6.97 (m, 2H, phenyl CH), 6.83-6.90 (m, 3H, phenyl CH), 3.77 (s, 3H, OCH3), 2.77-2.91 (m, 8H, piperazine CH2), 2.49-2.53 (m, 1H, NH). A solution of 9.55 g (0.0370 mol) of 4-cyclohexyl-3-methyl-4-oxo-3-phenylbutyraldehyde in 10 mL of iPrOAc was added to 6.77 g (0.0352 mol) of neat 1-(2′-methoxyphenyl)piperazine. The mixture turned turbid, and then turned to a solid mass when 10 mL of iPrOAc was added. The solid was slurried with 45 mL of iPrOAc. After 1.5 h, reaction was complete. The solid was vacuum filtered and washed with 10 mL of iPrOAc and air dried to afford 9.81 g (64.4%) of pure enamine as an off-white powder. The filtrate was concentrated to afford 6.40 g of crude enamine;

後処理

  1. concentrationof concentrated (29.4%) NH4OH (aq) (pH=9)
  2. extractionThe mixture was extracted twice with 250 mL of 1:1 (v/v) of THF
  3. dry with materialdried over MgSO4, gravity
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-10b037e548274f3d9083259d845e504b
出典データセット
uspto-grants-2002_03
特許番号
US06358958B2

関連ノート

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