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Bis(2-chloroethyl)amine hydrochloride → 1-[4,5-Dimethoxy-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine

HRID 2218865
Notes
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Reaction equation

HRID 2218865 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([NH2:11])=[C:5]([CH:12]2[CH2:17][C:16]([CH3:19])([CH3:18])[CH2:15][C:14]([CH3:21])([CH3:20])[CH2:13]2)[CH:4]=1.Cl.Cl[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]Cl>ClC1C=CC=CC=1Cl>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([N:11]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[C:5]([CH:12]2[CH2:17][C:16]([CH3:19])([CH3:18])[CH2:15][C:14]([CH3:21])([CH3:20])[CH2:13]2)[CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 522769Bis(2-chloroethyl)amine hydrochlorideHCID 231418854,5-Dimethoxy-2-(3,3,5,5-tetramethylcyclohexyl)phenylamine

Product 1

HCID 231415391-[4,5-Dimethoxy-2-(3,3,5,5-tetramethylcyclohexyl)phenyl]piperazine

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
220 °C

Procedure

A mixture of the crude product of 4,5-dimethoxy-2-(3,3,5,5-tetramethylcyclohexyl)phenylamine produced in Example (87c), bis(2-chloroethyl)amine hydrochloride (700 mg, 3.91 mmol) and 1,2-dichlorobenzene (10 ml) was stirred for 2 hours at an external temperature of 220° C. During the reaction, nitrogen gas was blown in several times to remove the excess hydrogen chloride gas from the reactor. The reaction mixture was cooled to room temperature, saturated aqueous solution of sodium hydrogencarbonate was added and extraction was performed with chloroform. The aqueous layer was again extracted with chloroform, and the organic layers were combined, washed with brine and then 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/heptane) to give 490 mg of the title compound as a brown oil.

Workup

  1. customDuring the reaction, nitrogen gas
  2. customto remove the excess hydrogen chloride gas from the reactor
  3. temperatureThe reaction mixture was cooled to room temperature
  4. additionsaturated aqueous solution of sodium hydrogencarbonate was added
  5. extractionextraction
  6. extractionThe aqueous layer was again extracted with chloroform
  7. washwashed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationThe desiccant was filtered off
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-b8140628940a4687b607b52d3bd8bfe0
Source dataset
uspto-grants-2008_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07410971B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes