Hexahydro-1,4-diazepine → HCID 16795380, compound

HRID 412065Notes

Reaction equation

HRID 412065 reaction equation
Cl[C:2]1[N:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH:13]1[CH2:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>C(O)C>[N:13]1([C:2]2[N:12]=[CH:11][CH:10]=[CH:9][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 68163Hexahydro-1,4-diazepineHCID 2796614Ethyl chloronicotinate

Product 1

HCID 16795380HCID 16795380, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.0 g of ethyl 2-chloronicotinate were heated to reflux for 2 h with 21.6 g of homopiperazine in 150 ml of ethanol. After removing the solvent, the residue was partitioned between NaCl solution and ethyl acetate and the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were dried over magnesium sulfate and concentrated, 11.1 g (83%) of the product being obtained.

Workup

  1. customAfter removing the solvent
  2. customthe residue was partitioned between NaCl solution and ethyl acetate
  3. extractionthe aqueous phase was extracted several times with ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3463ca04b6eb4d278bd722214f9afce8
Source dataset
uspto-grants-2003_05
Patent number
US06562827B1

Reaction notes

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