Diisopropylethylamine → HCID 68683838, compound

HRID 2234502Notes

Reaction equation

HRID 2234502 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-])=O)[C:6](Cl)=[O:7].CCN(C(C)C)C(C)C.[NH2:24][CH:25]1[CH2:30][CH2:29][CH:28]([N:31]([CH3:33])[CH3:32])[CH2:27][CH2:26]1>C(Cl)Cl>[NH2:12][C:11]1[CH:10]=[CH:9][C:5]([C:6]([NH:24][CH:25]2[CH2:30][CH2:29][CH:28]([N:31]([CH3:33])[CH3:32])[CH2:27][CH2:26]2)=[O:7])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 345823N,N-Dimethyl-1,4-cyclohexanediamineHCID 111276553-methoxy-4-nitro-benzoyl Chloride2×

Product 1

HCID 68683838HCID 68683838, compoundYield 113.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-methoxy-4-nitro-benzoyl chloride (Intermediate 189; 1.0 g, 4.64 mmol) was dissolved in DCM (20 mL) and cooled on an ice bath. DIPEA (970 uL) was added dropwise. 1-amino-4-dimethylaminocyclohexane (ABChem. Inc.; 660 mg, 4.64 mmol) was dissolved in DCM (10 mL) and added to the reaction solution. The reaction mixture was brought back to room temperature and stirred for 2 hours. The reaction mixture was washed with brine and NaOH (aq). The organic layer was extracted by filtering through a PTFE cup and evaporated to yield the title compound as an orange solid (1.54 g, 100%).

Workup

  1. temperaturecooled on an ice bath
  2. additionadded to the reaction solution
  3. customwas brought back to room temperature
  4. washThe reaction mixture was washed with brine and NaOH (aq)
  5. extractionThe organic layer was extracted
  6. filtrationby filtering through a PTFE cup
  7. customevaporated

Sources & evidence

ORD record
ord-66c4c441c7964214ba3737e775230b53
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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