Bis(2-chloroethyl)amine hydrochloride → 1-[4-[(4-Fluorophenyl)methyl]phenyl]piperazine

HRID 1004126Notes

Reaction equation

HRID 1004126 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.Cl.Cl[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]Cl>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([N:13]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:14][CH:15]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 225999654-[(4-Fluorophenyl)methyl]aniline

Product 1

HCID 15199981-[4-[(4-Fluorophenyl)methyl]phenyl]piperazineYield 75%

Conditions

Temperature
100 °C

Procedure

A mixture of 500 mg of 4-(4-fluorophenyl)methylaniline and 445 mg of bis(2-chloroethyl)amine hydrochloride was stirred at 100° C. for two hours, then gradually raised in temperature and stirred at 200° C. for a further two hours. This was cooled to room temperature, then the product was purified by silica gel column chromatography (chloroform:methanol:water (2% acetic acid)=65:35:5) to obtain the above-referenced compound (10) in an amount of 503 mg (yield 75%).

Workup

  1. temperaturegradually raised in temperature
  2. stirringstirred at 200° C. for a further two hours
  3. temperatureThis was cooled to room temperature
  4. customthe product was purified by silica gel column chromatography (chloroform:methanol:water (2% acetic acid)=65:35:5)

Sources & evidence

ORD record
ord-7c4ac2d0e9eb4c8d82cd887b829d7bb0
Source dataset
uspto-grants-2000_04
Patent number
US06048876

Reaction notes

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