Sodium Hydroxide → 2-Phenylpiperazine

HRID 482479ノート

反応式

HRID 482479 の反応式
[C:1]1([C:7]2[CH:12]=[N:11][CH:10]=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>C(O)(=O)C.O>[C:1]1([CH:7]2[CH2:12][NH:11][CH2:10][CH2:9][NH:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 2

HCID 14798Sodium HydroxideHCID 642870Pyrazine, 2-phenyl-

生成物 1

HCID 2506732-Phenylpiperazine収率 59.5%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

To a solution of 2-phenylpyrazine (11.64 gram, 74.53 mmol) in acetic acid (58.2 ml) was added palladium acetate Pd(OAc)2 (2.33 gram, 9.94 mmol). The mixture was hydrogenated at 50 psi for four hours. After the reaction was complete, the catalyst was filtered off and rinsed with a small portion of acetic acid. The filtrate was concentrated under house vacuum to give a brown-black solid which was suspended in deionized water (300 ml) and adjusted to pH 13 with 20% NaOH solution. The product was extracted from aqueous solution with EtOAc (200 ml, 3×), dried over MgSO4, filtered and evaporated to dryness to give 2-phenylpiperazine (7.2 gram). An additional 1.6 g of 2-phenylpiperazine was obtained by evaporating the aqueous fraction to a solid and triturating the solid with CH2Cl2. Total yield of 2-phenylpiperazine was 73%. The crude material was crystallized from EtOAc and hexane for characterization, m.p. 86°-88° C.; FAB mass [M+1]+ 163; Found, C, 74.04; H, 8.66; N, 17.15. Calcd. for C10H14N2, C, 74.04; H. 8.69; N, 17.26.

後処理

  1. filtrationthe catalyst was filtered off
  2. washrinsed with a small portion of acetic acid
  3. concentrationThe filtrate was concentrated under house vacuum
  4. customto give a brown-black solid which
  5. extractionThe product was extracted from aqueous solution with EtOAc (200 ml, 3×)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated to dryness

出典と根拠

ORDレコード
ord-26b974564c8c41468ecfdaa6336afe59
出典データセット
uspto-grants-1998_08
特許番号
US05798359

反応ノート

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