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

HRID 32143

反応式

HRID 32143 の反応式
[CH2:1]([C:3]1([CH2:18][CH3:19])[CH2:8][CH2:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=2[NH2:17])=[CH:5][CH2:4]1)[CH3:2].Cl.Cl[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]Cl>ClC1C=CC=CC=1Cl>[CH2:18]([C:3]1([CH2:1][CH3:2])[CH2:8][CH2:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=2[N:17]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:5][CH2:4]1)[CH3:19]

参加物

4

反応物 2

HCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 231430132-(4,4-Diethylcyclohex-1-enyl)-5-methoxyphenylamine

生成物 1

HCID 231420331-[2-(4,4-Diethylcyclohex-1-enyl)-5-methoxyphenyl]piperazine収率 42.6%

試薬・触媒・溶媒 1

HCID 72391,2-Dichlorobenzene溶媒

実験手順

A solution of 2-(4,4-diethylcyclohex-1-enyl)-5-methoxyphenylamine (2.6 g, 10 mmol) prepared in Example (6e) and bis(2-chloroethyl)amine hydrochloride (2.2 g, 12 mmol) in 1,2-dichlorobenzene (10 mL) was stirred at an external temperature of 210° C. Nitrogen gas was blown into the reactor several times during the reaction to remove the excess hydrogen chloride gas in the reactor. After 1 hour, the reaction mixture was cooled to room temperature, and then 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 1.4 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-c6bfcad68c2e4b45b6f0c4a38b7560d9
出典データセット
uspto-grants-2008_09
特許番号
US07425554B2

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