1-Butanol → 4-(Piperazin-1-yl)benzonitrile hydrochloride

HRID 1533896ノート

反応式

HRID 1533896 の反応式
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+].C(O)CCC.[ClH:27]>C(OCC)(=O)C>[ClH:27].[N:10]1([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1

参加物

7

反応物 5

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 4837PiperazineHCID 11430Potassium CarbonateHCID 12162Benzonitrile, 4-bromo-

生成物 1

HCID 27339944-(Piperazin-1-yl)benzonitrile hydrochloride

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 27.3 g (0.15 mol) of p-bromobenzonitrile, 38.7 g (0.45 mol) of piperazine and 42.0 g (0.30 mol) of solid potassium carbonate in a total volume of 60 mL of n-butanol was heated at reflux for 6 h under a nitrogen atmosphere. The mixture was concentrated under reduced pressure and the slurry partitioned between 10% sodium hydroxide and chloroform. The chloroform layer was separated, dried (MgSO4) and concentrated under reduced pressure to give an oil. The oil was eluted through a 400 g silica gel column with a 10% methanol in methylene chloride mixture. The appropriate fractions were concentrated under reduced pressure to give a golden oil. Trituration of this oil with ethyl acetate gave a white powder. The collected white powder was stirred for 15 min in ethereal HCl and recrystallized from methanol-water to give 1.5 g (4.5%)* of white solid, mp>160° C. with decomposition.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 6 h under a nitrogen atmosphere
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customthe slurry partitioned between 10% sodium hydroxide and chloroform
  5. customThe chloroform layer was separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customto give an oil
  9. washThe oil was eluted through a 400 g silica gel column with a 10% methanol in methylene chloride mixture
  10. concentrationThe appropriate fractions were concentrated under reduced pressure
  11. customto give a golden oil
  12. customrecrystallized from methanol-water
  13. customto give 1.5 g (4.5%)* of white solid, mp>160° C. with decomposition

出典と根拠

ORDレコード
ord-eb9d6a48629145e493d5e338fdbf6363
出典データセット
uspto-grants-1992_02
特許番号
US05086055

反応ノート

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