Triethylamine → HCID 15941168, compound

HRID 365300Notes

Reaction equation

HRID 365300 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.C(N(CC)CC)C.[NH:21]1[CH2:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>C(O)C>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[CH2:3][N:21]1[CH2:27][CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 68163Hexahydro-1,4-diazepineHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 15941168HCID 15941168, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After a mixture consisting of 2-chloromethyl-quinoline hydrochloride (63.16 g, 295 mmol), triethyl-amine (29.85 g, 295 mmol), homopiperazine (50.08 g, 591 mmol) and ethanol (600 ml) was stirred at room temperature for 2 days, the solvent was distilled off under reduced pressure. Water was added to the residue. After the resulting mixture was washed three times with ethyl ether, sodium chloride was added to the water layer, followed by extraction four times with chloroform-methanol (2:1). The extract was washed with an aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, whereby 28.00 g of the title compound were obtained as a yellow oil (yield: 39.3%).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionWater was added to the residue
  3. washAfter the resulting mixture was washed three times with ethyl ether, sodium chloride
  4. additionwas added to the water layer
  5. extractionfollowed by extraction four times with chloroform-methanol (2:1)
  6. washThe extract was washed with an aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-81caef4093fa442c9c32575e3bed6bc2
Source dataset
uspto-grants-2000_10
Patent number
US06127360

Reaction notes

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