Thionyl Chloride → HCID 22469796, compound

HRID 395017Notes

Reaction equation

HRID 395017 reaction equation
S(Cl)([Cl:3])=O.[F:5][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[CH2:16][CH2:17][CH2:18][C:19]1([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24][CH2:23][N:22]([CH2:25][CH2:26]O)[CH2:21][CH2:20]1)=[CH:13][C:12]([O:33][CH3:34])=[CH:11][CH:10]=2>ClCCl>[ClH:3].[ClH:3].[Cl:3][CH2:26][CH2:25][N:22]1[CH2:23][CH2:24][C:19]([CH2:18][CH2:17][CH2:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([O:33][CH3:34])[CH:13]=3)[N:8]=[CH:7][C:6]=2[F:5])([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:20][CH2:21]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22469117HCID 22469117, compound

Product 1

HCID 22469796HCID 22469796, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

5.73 cm3 of thionyl chloride were added dropwise to a suspension of 0.6 g of ethyl 4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]-1-(2-hydroxyethyl)piperidine-4-carboxylate in 10 cm3 of dichloromethane with stirring in the region of 20° C., and the mixture was stirred for 24 hours at a temperature in the region of 20° C. The reaction mixture was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The residue was taken up in 3 times 30 cm3 of cyclohexane and evaporated to dryness as under the above conditions. 0.67 g of ethyl 1-(2-chloroethyl)-4-[3-(3-fluoro-6-methoxyquinolin-4-yl)propyl]piperidine-4-carboxylate dihydrochloride was obtained in the form of a beige-colored solid.

Workup

  1. stirringthe mixture was stirred for 24 hours at a temperature in the region of 20° C
  2. concentrationThe reaction mixture was concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  3. customevaporated to dryness as under the above conditions

Sources & evidence

ORD record
ord-6191807235c448f48d51f91e83eb4c05
Source dataset
uspto-grants-2003_08
Patent number
US06603005B2

Reaction notes

Loading…