HCID 45084195, compound → {3-[Bis(4-methoxybenzyl)amino]-4-chlorophenyl}(1-methylcyclopropyl)methanone

HRID 2402346Notes

Reaction equation

HRID 2402346 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:24](I)=[CH:23][C:3]=1[N:4]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.C([Mg]Cl)(C)C.CON(C)[C:36]([C:38]1([CH3:41])[CH2:40][CH2:39]1)=[O:37]>C1COCC1.C(OCC)C>[CH3:13][O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][N:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[C:3]2[CH:23]=[C:24]([C:36]([C:38]3([CH3:41])[CH2:40][CH2:39]3)=[O:37])[CH:25]=[CH:26][C:2]=2[Cl:1])=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 45084195HCID 45084195, compoundHCID 708733002-Chloro-5-iodo-N,N-bis(4-methoxybenzyl)anilineHCID 178418918HCID 178418918, compound

Product 1

HCID 70873254{3-[Bis(4-methoxybenzyl)amino]-4-chlorophenyl}(1-methylcyclopropyl)methanone

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Under argon, 7.587 g (15.37 mmol) of 2-chloro-5-iodo-N,N-bis(4-methoxybenzyl)aniline were dissolved in 100 ml of THF and cooled to −78° C. 7.65 ml (15.27 mmol) of a 2 M solution of isopropylmagnesium chloride in diethyl ether were then slowly added dropwise. The reaction solution was then slowly warmed to −40° C. and stirred at this temperature for 30 min. 2 g (13.97 mmol) of N-methoxy-N,1-dimethylcyclopropanecarboxamide [R. Shintani et al., Chem. Eur. J., 15 (35), 8692-8694 (2009)], dissolved in 20 ml of THF, were then slowly added dropwise to the reaction solution. The reaction mixture obtained was then slowly warmed to room temperature and stirred at this temperature overnight. 50 ml of an ice-cold saturated aqueous ammonium chloride solution were then added to the reaction mixture. After separation of the phases, the aqueous phase was extracted three more times with ethyl acetate, and the combined organic phases were dried over magnesium sulphate, filtered and evaporated to dryness. The crude product obtained was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 10:1). This gave 3.977 g (63% of theory) of the title compound.

Workup

  1. temperatureThe reaction solution was then slowly warmed to −40° C.
  2. additionwere then slowly added dropwise to the reaction solution
  3. customThe reaction mixture obtained
  4. temperaturewas then slowly warmed to room temperature
  5. stirringstirred at this temperature overnight
  6. customAfter separation of the phases
  7. extractionthe aqueous phase was extracted three more times with ethyl acetate
  8. dry with materialthe combined organic phases were dried over magnesium sulphate
  9. filtrationfiltered
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-89f1265449524566aad48ba487069e1c
Source dataset
uspto-grants-2014_08
Patent number
US08796335B2

Reaction notes

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