Triethylamine → HCID 18180103, compound

HRID 1358933Notes

Reaction equation

HRID 1358933 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(CC)CC)C.[CH:25]1([C:28](Cl)=[O:29])[CH2:27][CH2:26]1>ClCCl>[CH:25]1([C:28]([N:15]2[CH2:16][CH2:17][N:12]([C:4]3[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[CH2:13][CH2:14]2)=[O:29])[CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 37831381-(2-methoxy-5-nitrophenyl)piperazine

Product 1

HCID 18180103HCID 18180103, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(2-methoxy-5-nitrophenyl)-piperazine (500 mg, 2.1 mmol) in dichloromethane (50 ml) at 0° C. under argon was added triethylamine (0.59 ml, 4.2 mmol) and cyclopropane carbonyl chloride (2.1 mmol). Stirring was continued for 12 hrs. The reaction mixture was concentrated in vacuo and partitioned between saturated aqueous NaHCO3 and dichloromethane. The organic layer was dried over sodium sulphate and concentrated in vacuo to give the title compound (D17) in 90% yield. Found MH+ 306.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned between saturated aqueous NaHCO3 and dichloromethane
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-46d7770d49514703bda5069c930a6f33
Source dataset
uspto-grants-2003_07
Patent number
US06599904B2

Reaction notes

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