1-Chloroethyl chloroformate → HCID 10519055, compound

HRID 361869Notes

Reaction equation

HRID 361869 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:27][CH3:28])[C:15]2[C:20]([NH:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:19][CH:18]=[C:17]([Cl:26])[N:16]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>C(Cl)Cl>[CH2:27]([N:14]([CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)[C:15]1[C:20]([NH:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[CH:19][CH:18]=[C:17]([Cl:26])[N:16]=1)[CH3:28]

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 10716019HCID 10716019, compound

Product 1

HCID 10519055HCID 10519055, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Benzyl-4-[N-ethyl-N-(3-(1,1-dimethylethylamino)-6-chloro-2-pyridinyl)amino]piperidine (EXAMPLE 269, 1.5 g) is dissolved in 8 ml of methylene chloride and cooled to 0°. Then 1-chloroethyl chloroformate (0.54 ml) is added dropwise. The reaction is warmed to 20°-25° and refluxed for 30 min. Then the reaction is concentrated under reduced pressure and 15 ml of methanol is added and the reaction is heated to reflux for 2 hr. Then it is poured into saturated aqueous sodium bicarbonate and extracted with chloroform. The organic extracts are dried over potassium carbonate and concentrated under reduced pressure. Purification by flash column chromatography (90:9.5:0.5; chloroform/methanol/concentrated ammonium hydroxide) gives the title compound.

Workup

  1. temperaturecooled to 0°
  2. temperatureThe reaction is warmed to 20°-25°
  3. temperaturerefluxed for 30 min
  4. concentrationThen the reaction is concentrated under reduced pressure and 15 ml of methanol
  5. additionis added
  6. temperaturethe reaction is heated
  7. temperatureto reflux for 2 hr
  8. additionThen it is poured into saturated aqueous sodium bicarbonate
  9. extractionextracted with chloroform
  10. dry with materialThe organic extracts are dried over potassium carbonate
  11. concentrationconcentrated under reduced pressure
  12. customPurification by flash column chromatography (90:9.5:0.5; chloroform/methanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-23210baf97b24e5aaa2b03dac2c9e9a3
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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