Hydrochloric Acid → HCID 20670032, compound

HRID 1532317Notes

Reaction equation

HRID 1532317 reaction equation
[NH2:1][C:2]1[C:3]([Cl:22])=[C:4]([CH:19]=[CH:20][CH:21]=1)[C:5]([NH:7][CH2:8][C:9]12[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2)=[O:6].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:31][CH2:32][N:33]([CH3:35])[CH3:34].Cl>O>[Cl:22][C:3]1[C:2]([NH:1][CH2:31][CH2:32][N:33]([CH3:35])[CH3:34])=[CH:21][CH:20]=[CH:19][C:4]=1[C:5]([NH:7][CH2:8][C:9]12[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2)=[O:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 20670051HCID 20670051, compound

Product 1

HCID 20670032HCID 20670032, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
138 °C

Procedure

A mixture of the amino compound from Example 54 (0.10 g), potassium carbonate (0.087 g) and N-(2-chloroethyldimethylamine hydrochloride was stirred and heated at 138° C. for 72 hr. The residue was dissolved in water and the product extracted into ethyl acetate. The organic extract was washed with brine, dried over sodium sulphate (Na2SO4) and concentrated to give an oil which was purified by Supercritical Fluid Chromatography eluting with CO2/methanol/0.1% diethylamine to give an oil. Addition of excess ethereal hydrogen chloride solution gave a solid which was triturated under an ether/ethanol/dichloromethane mixture to give a colourless powder (0.04 g).

Workup

  1. extractionthe product extracted into ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried over sodium sulphate (Na2SO4)
  5. concentrationconcentrated
  6. customto give an oil which
  7. customwas purified by Supercritical Fluid Chromatography
  8. washeluting with CO2/methanol/0.1% diethylamine
  9. customto give an oil
  10. customgave a solid which
  11. customwas triturated under an ether/ethanol/dichloromethane mixture

Sources & evidence

ORD record
ord-32fae5d0ba884003b6d060c2b6cf9794
Source dataset
uspto-grants-2001_03
Patent number
US06201024B1

Reaction notes

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