Bis(2-chloroethyl)amine hydrochloride → 1-[2-(3,3,4,4-Tetramethylcyclopent-1-enyl)phenyl]piperazine

HRID 32170Notes

Reaction equation

HRID 32170 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[CH2:5][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[NH2:15])=[CH:3]1.Cl.Cl[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]Cl>ClC1C=CC=CC=1Cl>[CH3:1][C:2]1([CH3:16])[C:6]([CH3:7])([CH3:8])[CH2:5][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:15]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)=[CH:3]1

Participants

4

Reactant 2

HCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 231419622-(3,3,4,4-Tetramethylcyclopent-1-enyl)phenylamine

Product 1

HCID 231425251-[2-(3,3,4,4-Tetramethylcyclopent-1-enyl)phenyl]piperazineYield 50.9%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 2-(3,3,4,4-tetramethylcyclopent-1-enyl)phenylamine (331 mg, 1.54 mmol) produced in Example (54c), 1,2-dichlorobenzene (4.7 mL) and bis(2-chloroethyl)amine hydrochloride (330 mg, 1.85 mmol) was stirred for 9 hours at an external temperature of 200° C. under a nitrogen atmosphere. During the reaction, a nitrogen stream was blown into the reactor several times to remove the hydrogen chloride gas in the reactor. The reaction mixture was air-cooled to room temperature, and then aqueous solution of potassium carbonate, ethyl acetate and methanol were added 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 obtained residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 223 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 reaction mixture was air-cooled to room temperature
  4. additionaqueous solution of potassium carbonate, ethyl acetate and methanol were added
  5. extractionextraction
  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)

Sources & evidence

ORD record
ord-24020421f68b400c9664d7a1a65f3fff
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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