1-Chloroethyl chloroformate → HCID 10660595, compound

HRID 361846Notes

Reaction equation

HRID 361846 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:26])[C:15]2[C:20]([NH:21][CH:22]([CH3:24])[CH3:23])=[CH:19][CH:18]=[C:17]([Cl:25])[N:16]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)=O)C.CO.C1(C)C=CC=CC=1>ClCCl>[CH3:26][N:14]([CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[C:15]1[C:20]([NH:21][CH:22]([CH3:24])[CH3:23])=[CH:19][CH:18]=[C:17]([Cl:25])[N:16]=1

Participants

5

Reactant 3

HCID 5213051-Chloroethyl chloroformateHCID 10690708HCID 10690708, compoundHCID 21867641Toluene methanol

Product 1

HCID 10660595HCID 10660595, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Benzyl-4-[N-methyl-N-(3-isopropylamino-6-chloro-2-pyridinyl)amino]piperidine (EXAMPLE 184, 1.60 g, 4.84 mmol) is dissolved in dichloromethane (0.2M) and cooled to 0°. 1-Chloroethyl-chloroformate (0.57 ml, 5.32 mmol) is added dropwise. The mixture is allowed to warm to 20°-25°, then refluxed one half hour. The solvent is removed to one third volume, 15 ml methanol is added and the mixture is refluxed 2 hr. Extraction with chloroform, drying the extract over sodium sulfate and removal of the solvent gives the crude product. Flash column chromatography (silica gel, 100 g; methanol/chloroform (10/90)) gives the title compound, NMR (300 MHz, CD3OD) 6.88, 3.49, 3.23, 2.87, 2.50, 1.95, 1.70 and 1.12δ.

Workup

  1. temperaturecooled to 0°
  2. temperatureto warm to 20°-25°
  3. temperaturerefluxed one half hour
  4. customThe solvent is removed to one third volume, 15 ml methanol
  5. additionis added
  6. temperaturethe mixture is refluxed 2 hr
  7. extractionExtraction with chloroform
  8. customdrying the
  9. extractionextract over sodium sulfate and removal of the solvent
  10. customgives the crude product

Sources & evidence

ORD record
ord-993a29fdac1e482bbd65318500da82cd
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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