Diisobutylaluminum hydride → 2-(3,4-Dichlorophenyl)piperazine

HRID 1602133

反応式

HRID 1602133 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[N:13][CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].CC(C[AlH]CC(C)C)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][NH:13][CH2:12][CH2:11][NH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

4

反応物 2

HCID 14487Diisobutylaluminum hydrideHCID 155946712-(3,4-Dichlorophenyl)pyrazine

生成物 1

HCID 42313562-(3,4-Dichlorophenyl)piperazine収率 40%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-(3,4-dichlorophenyl)pyrazine (10 g, 44.43 mmol) in dry THF (150 ml) was added slowly a solution of DIBAL-H (1 M in THF, 444.3 ml) through a dropping funnel at 10° C. under N2. The color of solution turned into red wine at the end of addition. The solution was gradually warmed up to room temperature overnight. After completion (checked by TLC) the reaction was quenched slowly by the addition of saturated Na2SO4 solution until no more H2 evolved. White precipitate was formed after stirring for 1.0 h. The precipitate was filtered off, rinsed with THF, dried over MgSO4 and evaporated to dryness. The crude material (10 g) was purified by flash chromatography on 300 g of flash grade silica gel in 7.5% NH3-MeOH/CH2Cl2 to give 4.11 g (17.77 mmol, 40%) of 2-(3,4-dichloro-phenyl)piperazine. m.p. 74-76° C.; FAB mass [M+1]+35Cl 231.

後処理

  1. additionThe color of solution turned into red wine at the end of addition
  2. customAfter completion (checked by TLC) the reaction was quenched slowly by the addition of saturated Na2SO4 solution until no more H2
  3. customWhite precipitate was formed
  4. filtrationThe precipitate was filtered off
  5. washrinsed with THF
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. customThe crude material (10 g) was purified by flash chromatography on 300 g of flash grade silica gel in 7.5% NH3-MeOH/CH2Cl2

出典と根拠

ORDレコード
ord-6355b1d7830444c1a4e1a75b46ac3f2b
出典データセット
uspto-grants-1999_11
特許番号
US05981520

関連ノート

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