1-Chloroethyl chloroformate → HCID 21462970, compound

HRID 1940554Notes

Reaction equation

HRID 1940554 reaction equation
C([N:8]1[CH2:13][CH:12]=[C:11]([CH2:14][CH2:15][C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)=O)C>ClCCl>[O:17]1[CH:18]=[CH:19][CH:20]=[C:16]1[CH2:15][CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 21462998HCID 21462998, compound

Product 1

HCID 21462970HCID 21462970, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A cooled (0° C.) solution of 1-benzyl-4-(2-[furan-2-yl]ethyl)-1,2,3,6-tetrahydropyridine (1.8 g, 6.8 mmol) in anhydrous dichloromethane (20 ml) was treated with 1-chloroethylchloroformate (0.95 ml, 8.8 mmol) dropwise. The mixture was stirred for 1 hr at 0° C. The solvent was evaporated and the residue dissolved in methanol (60 ml). This solution was heated at reflux for one hour whereupon the solvent was evaporated. The residue was partitioned between dichloromethane and saturated aqueous potassium carbonate solution. The organic phase was separated, dried (Na2 SO4) and evaporated to give the title compound (867 mg, 72%) as a colourless oil; δH (DMSO-d6) 1.84-1.96 (2H, m, tetrahydropyridinyl CH2), 2.16-2.30 (2H, m, CH2), 2.64-2.80 (4H, m, tetrahydropyridinyl CH2 and CH2), 3.06-3.10 (2H, m, tetrahydropyridinyl CH2), 5.40-5.46 (1H, m, tetrahydropyridinyl 5-H), 6.06-6.12 (1H, m, furanyl H), 6.32-6.38 (1H, m, furanyl H), and 7.48-7.56 (1H, m, furanyl H).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in methanol (60 ml)
  3. temperatureThis solution was heated
  4. temperatureat reflux for one hour whereupon the solvent
  5. customwas evaporated
  6. customThe residue was partitioned between dichloromethane and saturated aqueous potassium carbonate solution
  7. customThe organic phase was separated
  8. customdried (Na2 SO4)
  9. customevaporated

Sources & evidence

ORD record
ord-3ff16775d8524c72876cdf715dcbd7c9
Source dataset
uspto-grants-1997_12
Patent number
US05700809

Reaction notes

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