Hydrochloric Acid → Piperazine, 1-[4-bromo-2-(1,1-dimethylethyl)phenyl]-, hydrochloride (1:2)

HRID 534822ノート

反応式

HRID 534822 の反応式
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:3]=1.[ClH:13].[Cl:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19]Cl.[OH-].[Na+].Cl>COCCOCCOC.C(OCC)(=O)C.CCOCC>[ClH:14].[ClH:13].[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:3]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 119590004-bromo-2-tert-butylphenylamine

生成物 1

HCID 66751142Piperazine, 1-[4-bromo-2-(1,1-dimethylethyl)phenyl]-, hydrochloride (1:2)収率 40%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8150Diglyme溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
170 °C

実験手順

A suspension of 4-bromo-2-tert-butylaniline (Reference Example 8, 25.0 g, 110 mmol) and bis(2-chloroethyl)amine hydrochloride (21.5 g, 120 mmol) in diethylene glycol dimethyl ether (157 mL) was stirred for 3 days at 170° C. It was cooled to room temperature, added 1 M sodium hydroxide solution (50 mL), and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give crude product. It was diluted with ethyl acetate and ether (50:50) and added 1 M hydrochloric acid solution to provide 1-(4-bromo-2-tert-butylphenyl)piperazine dihydrochloride (16.2 g, 40%) as a gray solid.

後処理

  1. temperatureIt was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give crude product

出典と根拠

ORDレコード
ord-aded8697d3b843e78c6180e5a9014580
出典データセット
uspto-grants-2014_10
特許番号
US08853215B2

反応ノート

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