Bis(2-chloroethyl)amine hydrochloride → 1-(2-Cycloheptylphenyl)piperazine

HRID 32153

반응식

HRID 32153 반응식
[CH:1]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH2:14])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.Cl[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]Cl>ClC1C=CC=CC=1Cl>[CH:1]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

참가 물질

4

반응물 2

HCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 109432572-Cycloheptylphenylamine

생성물 1

HCID 231425011-(2-Cycloheptylphenyl)piperazine수율 73.3%

시약·촉매·용매 1

HCID 72391,2-Dichlorobenzene용매

반응 조건

온도
200 °C

실험 절차

To a solution of the 2-cycloheptylphenylamine (539 mg, 2.85 mmol) produced in Example (44b) in 1,2-dichlorobenzene (7 mL) was added bis(2-chloroethyl)amine hydrochloride (610 mg, 3.42 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 8 hours, the mixture was air-cooled to room temperature. To the reaction mixture were added aqueous solution of potassium carbonate, ethyl acetate and methanol, and extraction was performed three times with ethyl acetate. The obtained organic layers were dried over anhydrous sodium sulfate, and then the desiccant was filtered off and the filtrate was concentrated under reduced pressure. The obtained residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 540 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. additionTo the reaction mixture were added aqueous
  5. extractionsolution of potassium carbonate, ethyl acetate and methanol, and extraction
  6. dry with materialThe obtained organic layers were dried over anhydrous sodium sulfate
  7. filtrationthe desiccant was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe obtained residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

출처 및 근거

ORD 기록
ord-85def35424e842e8986fd743e9dd6d5a
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425554B2

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