1-Chloroethyl chloroformate → HCID 18942185, compound

HRID 355393Notes

Reaction equation

HRID 355393 reaction equation
C([N:8]1[CH2:13][CH:12]=[C:11](/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[Cl:23]C(OC(Cl)C)=O>ClCCl>[ClH:23].[F:22][C:19]1[CH:20]=[CH:21][C:16](/[CH:15]=[CH:14]/[C:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 18942180HCID 18942180, compound

Product 1

HCID 18942185HCID 18942185, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (E)-1-benzyl-4-[2-(4-fluorophenyl)ethenyl]-1,2,3,6-tetrahydropyridine (11.6 g, 37.5 mmol) in dichloromethane (500 ml) at 0° C. was added 1-chloroethyl chloroformate (4.85 ml, 45 mmol). The reaction was stirred initially at 0° C., and allowing it to warm to room temperature over 2 hours. The solvent was evaporated and methanol (500 ml) added. The mixture was heated at reflux for 1 hour, cooled to room temperature, and the solvent evaporated to a slurry. Diethyl ether was added and the resultant precipitate filtered and dried to yield (E)-4-[2-(4-fluorophenyl)ethenyl]-1,2,3,6-tetrahydropyridine hydrochloride (6.2 g, 69%) as a white solid. δH (DMSO-d6) 2.49-2.53 (2H, m, tetrahydropyridinyl CH2), 3.23 (2H, t, J 6.1 Hz, tetrahydropyridinyl CH2), 3.69 (2H, br s, tetrahydropyridinyl CH2), 5.90 (1H, br s, tetrahydropyridinyl 5-CH), 6.61 (1H, d, J 16.3 Hz, ArCHCHC), 6.92 (1H, d, J 16.3 Hz, ArCHCHC), 7.15-7.20 (2H, m, ArH), 7.55-7.59 (7H, m, ArH) and 9.45 (1H, br s, NH).

Workup

  1. temperatureto warm to room temperature over 2 hours
  2. customThe solvent was evaporated
  3. additionmethanol (500 ml) added
  4. temperatureThe mixture was heated
  5. temperatureat reflux for 1 hour
  6. temperaturecooled to room temperature
  7. customthe solvent evaporated to a slurry
  8. additionDiethyl ether was added
  9. filtrationthe resultant precipitate filtered
  10. customdried

Sources & evidence

ORD record
ord-74e86e46408d47a0881ce12a7ed49b67
Source dataset
uspto-grants-1998_11
Patent number
US05830901

Reaction notes

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