Bis(2-chloroethyl)amine hydrochloride → 1-(2-Cyclooct-1-enylphenyl)piperazine

HRID 32156

반응식

HRID 32156 반응식
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH2:15])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.Cl.Cl[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]Cl>ClC1C=CC=CC=1Cl>[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

참가 물질

4

반응물 2

HCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 539879012-Cyclooct-1-enylphenylamine

생성물 1

HCID 692189821-(2-Cyclooct-1-enylphenyl)piperazine수율 53.2%

시약·촉매·용매 1

HCID 72391,2-Dichlorobenzene용매

반응 조건

온도
200 °C

실험 절차

To a solution of 2-cyclooct-1-enylphenylamine (140 mg, 0.695 mmol) in 1,2-dichlorobenzene (2 mL) was added bis(2-chloroethyl)amine hydrochloride (149 mg, 0.835 mmol), and the mixture was stirred at an external temperature of 200° C. under a nitrogen atmosphere. During the reaction, a nitrogen stream was blown into the reactor to remove the hydrogen chloride gas in the reactor. This procedure was repeated several times. After 9 hours, the mixture was air-cooled to room temperature. Aqueous solution of potassium carbonate, ethyl acetate and methanol were added to the reaction mixture and extraction was performed three times with ethyl acetate. The obtained organic layers were dried over anhydrous sodium 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/heptane) to give 100 mg of the title compound as a brown oil.

후처리

  1. customDuring the reaction
  2. customto remove the hydrogen chloride gas in the reactor
  3. temperaturethe mixture was air-cooled to room temperature
  4. additionAqueous solution of potassium carbonate, ethyl acetate and methanol were added to the reaction mixture and extraction
  5. dry with materialThe obtained organic layers were dried over anhydrous sodium 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/heptane)

출처 및 근거

ORD 기록
ord-849380cad0864351947609535eddc05f
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425554B2

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