Sodium Bicarbonate → HCID 23142789, compound

HRID 2218859Notes

Reaction equation

HRID 2218859 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([CH:10]2[CH2:15][C:14]([CH3:17])([CH3:16])[CH2:13][C:12]([CH3:19])([CH3:18])[CH2:11]2)[CH:4]=1.Cl.Cl[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]Cl.C(=O)([O-])O.[Na+]>ClC1C=CC=CC=1Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[C:5]([CH:10]2[CH2:15][C:14]([CH3:17])([CH3:16])[CH2:13][C:12]([CH3:19])([CH3:18])[CH2:11]2)[CH:4]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 522769Bis(2-chloroethyl)amine hydrochloride2×HCID 231421244-Methoxy-2-(3,3,5,5-tetramethylcyclohexyl)phenylamine

Product 1

HCID 23142789HCID 23142789, compound

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Conditions

Temperature
220 °C

Procedure

A mixture of the crude product of 4-methoxy-2-(3,3,5,5-tetramethylcyclohexyl)phenylamine produced in Example (85b), bis(2-chloroethyl)amine hydrochloride (770 mg, 4.33 mmol) and 1,2-dichlorobenzene (10 ml) was stirred for 2 hours at an external temperature of 220° C. During the reaction, the excess hydrogen chloride gas in the reactor was removed several times with nitrogen gas. Bis(2-chloroethyl)amine hydrochloride (180 mg, 1.01 mmol) was then added and the mixture was stirred for 1 hour under the same conditions. 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 660 mg of the title compound as a brown solid.

Workup

  1. customDuring the reaction
  2. customthe excess hydrogen chloride gas in the reactor was removed several times with nitrogen gas
  3. stirringthe mixture was stirred for 1 hour under the same conditions
  4. temperatureThe reaction mixture was cooled to room temperature
  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-681824e9b1ed474ba7c79cfbe917f57b
Source dataset
uspto-grants-2008_08
Patent number
US07410971B2

Reaction notes

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