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

HRID 32134

Reaction equation

HRID 32134 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=2[NH2:16])=[CH:4][CH2:3]1.Cl.Cl[CH2:20][CH2:21][NH:22][CH2:23][CH2:24]Cl>ClC1C=CC=CC=1Cl>[CH3:1][C:2]1([CH3:17])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=2[N:16]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[CH:4][CH2:3]1

Participants

4

Reactant 2

HCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 231419942-(4,4-Dimethylcyclohex-1-enyl)-5-methoxyphenylamine

Product 1

HCID 231420461-[2-(4,4-Dimethylcyclohex-1-enyl)-5-methoxyphenyl]piperazineYield 48.2%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of 2-(4,4-dimethylcyclohex-1-enyl)-5-methoxyphenylamine (3.35 g, 14.5 mmol) prepared in Example (1d) and bis(2-chloroethyl)amine hydrochloride (3.1 g, 17.4 mmol) in 1,2-dichlorobenzene (10 mL) was stirred at 210° C. for 30 minutes. Nitrogen gas was blown into the reactor several times during the reaction to remove the excess hydrogen chloride gas in the reactor. The reaction mixture was cooled to room temperature, 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 2.1 g of the title compound as a yellow oil.

Workup

  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)

Sources & evidence

ORD record
ord-c280af71f4f54b38a36eaeafd3efb966
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Linked notes

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