Bis(2-chloroethyl)amine hydrochloride → 1-[2-(4,4-Dimethylcyclohex-1-enyl)-5-methoxyphenyl]piperazine

HRID 32134

反応式

HRID 32134 の反応式
[CH3:1][C:2]1([CH3:17])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=2[NH2:16])=[CH:4][CH2:3]1.Cl.Cl[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]Cl>ClC1C=CC=CC=1Cl>[CH3:1][C:2]1([CH3:17])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=2[N:16]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[CH:4][CH2:3]1

参加物

4

反応物 2

HCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 231419942-(4,4-Dimethylcyclohex-1-enyl)-5-methoxyphenylamine

生成物 1

HCID 231420461-[2-(4,4-Dimethylcyclohex-1-enyl)-5-methoxyphenyl]piperazine収率 48.2%

試薬・触媒・溶媒 1

HCID 72391,2-Dichlorobenzene溶媒

実験手順

A solution of 2-(4,4-dimethylcyclohex-1-enyl)-5-methoxyphenylamine (3.35 g, 14.5 mmol) prepared in Example (1d) and bis(2-chloroethyl)amine hydrochloride (3.1 g, 17.4 mmol) in 1,2-dichlorobenzene (10 mL) was stirred at 210° C. for 30 minutes. Nitrogen gas was blown into the reactor several times during the reaction to remove the excess hydrogen chloride gas in the reactor. The reaction mixture was cooled to room temperature, saturated aqueous sodium hydrogencarbonate was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane) to give 2.1 g of the title compound as a yellow oil.

後処理

  1. customNitrogen gas was blown into the reactor several times during the reaction
  2. customto remove the excess hydrogen chloride gas in the reactor
  3. additionsaturated aqueous sodium hydrogencarbonate was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. filtrationThe desiccant was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-c280af71f4f54b38a36eaeafd3efb966
出典データセット
uspto-grants-2008_09
特許番号
US07425554B2

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