Dichloromethane → HCID 67582441, compound

HRID 343351Notes

Reaction equation

HRID 343351 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]=[C:11](/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=CC=[CH:4][CH:3]=1.ClC(O[CH:26]([Cl:28])[CH3:27])=O.[Cl:29]CCl>>[Cl:29][C:4]1[CH:3]=[C:2]([CH:7]=[CH:27][C:26]=1[Cl:28])[CH2:1][N:8]1[CH2:13][CH:12]=[C:11](/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 5213051-Chloroethyl chloroformateHCID 15818889HCID 15818889, compound

Product 1

HCID 67582441HCID 67582441, compoundYield 77%

Conditions

Temperature
0 °C

Procedure

To a solution of (E)-1-benzyl-4-(2-phenylethenyl)-1,2,3,6-tetrahydropyridine (27 g, 100 mmol) in dichloromethane (400 ml) at 0° C. was added 1-chloroethyl chloroformate (13 ml, 120 mmol) via syringe, keeping the temperature below 5° C. The reaction was stirred at 0° C. for 1 hour and then warmed to room temperature over 2 hours. The solvent was evaporated, methanol (500 ml ) added to the residue, and the reaction refluxed for 90 minutes. The reaction was cooled to room temperature, the solvent evaporated to a slurry and ether (≈200 ml) added. The resultant solid was filtered and dried to give the title compound (17 g, 77%); δH (DMSO-d6) 2.55 (2H, br s, tetrahydropyridinyl CH2), 3.25 (2H, br s, tetrahydropyridinyl CH2), 3.71 (2H, br s, tetrahydropyridinyl CH2), 5.92 (1H, br s, tetrahydropyridinyl 5-CH), 6.62 (1H, d, J 16.3 Hz, ArCH=CHC), 6.97 (1H, d, J 16.3 Hz, ArCH=CHC), 7.25 (1H, d, J 7.3 Hz, 4-H), 7.35 (2H, t, J 7.3 Hz, 3-H, 5-H), 7.52 (2H, d, J 7.3 Hz, 2-H, 6-H), and 9.51 (1H, br s, NH); m/z (ES+) 306 (M+1)+.

Workup

  1. customthe temperature below 5° C
  2. temperaturewarmed to room temperature over 2 hours
  3. customThe solvent was evaporated
  4. additionmethanol (500 ml ) added to the residue
  5. temperaturethe reaction refluxed for 90 minutes
  6. temperatureThe reaction was cooled to room temperature
  7. customthe solvent evaporated to a slurry and ether (≈200 ml)
  8. additionadded
  9. filtrationThe resultant solid was filtered
  10. customdried

Sources & evidence

ORD record
ord-ef7571e449d945eeafa7d181d8c59939
Source dataset
uspto-grants-1999_01
Patent number
US05861407

Reaction notes

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