1,1-Dichloroethane → 4-(4-Methoxyphenyl)-1,2,3,6-tetrahydropyridine

HRID 368837Notes

Reaction equation

HRID 368837 reaction equation
C([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.ClC(Cl)C.ClC(OC(Cl)=O)C>>[CH3:21][O:20][C:17]1[CH:16]=[CH:15][C:14]([C:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=2)=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 63651,1-DichloroethaneHCID 5213051-Chloroethyl chloroformateHCID 106364031-Benzyl-4-(4-methoxyphenyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 135448404-(4-Methoxyphenyl)-1,2,3,6-tetrahydropyridine

Procedure

A mixture of 1-benzyl-1,2,3,6-tetrahydro-4-(4-methoxyphenyl)pyridine (XVI, EXAMPLE 42-Step 2, 2.021 g, 7.2 mmol), dichloroethane (19 ml) and 1-chloroethylchloroformate (2.8 ml, 26.0 mmol) is refluxed overnight. The mixture is concentrated to about one third the original volume and methanol is added. The mixture is refluxed for 2 hr, then cooled and concentrated. The resulting solids are slurried in dichloromethane, ether is added, and the solids are collected and then partitioned between dichloromethane and saturated aqueous sodium bicarbonate. Some solids remained in the aqueous phase and are collected and combined with the organic fractions. Following chromatography on silica gel eluting with methanol/dichloromethane (0.5% ammonium hydroxide, 6/94), the appropriate fractions are pooled and concentrated to give 1,2,3,6-tetrahydro-4-(4-methoxypheny)pyridine (XVII).

Workup

  1. temperatureis refluxed overnight
  2. concentrationThe mixture is concentrated to about one third the original volume and methanol
  3. additionis added
  4. temperatureThe mixture is refluxed for 2 hr
  5. temperaturecooled
  6. concentrationconcentrated
  7. additionether is added
  8. customthe solids are collected
  9. custompartitioned between dichloromethane and saturated aqueous sodium bicarbonate
  10. customare collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-46235a4b1e5f4fefb4e7c05b173a0c87
Source dataset
uspto-grants-2000_10
Patent number
US06133446

Reaction notes

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