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

HRID 2218803

Reaction equation

HRID 2218803 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
200 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-f0a9864d89a849849b25cc56c19bc9ad
Source dataset
uspto-grants-2008_08
Patent number
US07410971B2

Linked notes

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