Thionyl Chloride → HCID 18928715, compound

HRID 1599474Notes

Reaction equation

HRID 1599474 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:23])[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9]1>C(Cl)(Cl)Cl>[Cl:3][CH2:6][CH2:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:23])[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 18928733HCID 18928733, compound

Product 1

HCID 18928715HCID 18928715, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
20 °C

Procedure

A solution of thionyl chloride (15.7 ml) in dry chloroform (100 ml) was added dropwise to a stirred solution of the product from Example 35 (51.1 g) in dry chloroform (500 ml) over 45 minutes, keeping the temperature between 0° C. and 5° C. The solution was allowed to warm to 20° C. with stirring and then heated under reflux for 2.5 hours. The mixture was cooled to 20° C., washed (saturated sodium bicarbonate solution, water), dried, filtered and evaporated to give 4-(2-chloroethyl)-1-(3-phenylpropionyl)piperidine as oil.

Workup

  1. customthe temperature between 0° C. and 5° C
  2. temperatureheated
  3. temperatureunder reflux for 2.5 hours
  4. temperatureThe mixture was cooled to 20° C.
  5. washwashed (saturated sodium bicarbonate solution, water)
  6. customdried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-a3a1819e3bba428eb7d039474baaaaf8
Source dataset
uspto-grants-1998_04
Patent number
US05741800

Reaction notes

Loading…