Thionyl Chloride → HCID 131723270, compound

HRID 2186351Notes

Reaction equation

HRID 2186351 reaction equation
S(Cl)([Cl:3])=O.[C:5]1([CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][C@@H:17]([CH2:20][CH2:21][CH:22](O)[C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[CH:31]=4)[N:26]=[CH:25][CH:24]=3)[C@@H:16]([C:36]([O:38][CH3:39])=[O:37])[CH2:15]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(Cl)(Cl)Cl>[C:5]1([CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][C@@H:17]([CH2:20][CH2:21][CH:22]([Cl:3])[C:23]3[C:32]4[C:27](=[CH:28][CH:29]=[C:30]([O:33][CH3:34])[CH:31]=4)[N:26]=[CH:25][CH:24]=3)[C@@H:16]([C:36]([O:38][CH3:39])=[O:37])[CH2:15]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 131723268HCID 131723268, compound

Product 1

HCID 131723270HCID 131723270, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

0.46 cm3 of thionyl chloride was added dropwise to a solution of 1 g of methyl (3R,4R)-1-(3-phenylpropyl)-4-[3-(R,S)-hydroxy-3-(6-methoxyquinolin-4-yl)-propyl]piperidine-3-carboxylate in 15 cm3 of chloroform while maintaining the temperature at 0° C. The reaction mixture was allowed to return to a temperature in the region of 20° C. with stirring over 2 hours. The reaction mixture was subsequently concentrated under reduced pressure (5 kPa) at a temperature in the region of 50° C. The residue was dissolved in 30 cm3 of distilled water and the aqueous phase was washed with 15 cm3 of dichloromethane, then basified to pH 9 with solid potassium carbonate and, finally, extracted with 3 times 20 cm3 of dichloromethane. The organic phases were combined, washed with 2 times 20 cm3 of distilled water, and dried over magnesium sulfate. After filtering and then concentrating under reduced pressure (5 kPa) at a temperature in the region of 45° C., 1.16 g of methyl (3R,4R)-1-(3-phenylpropyl)-4-[3-(R,S)-chloro-3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylate were obtained in the form of a brown oil.

Workup

  1. customto return to a temperature in the region of 20° C.
  2. concentrationThe reaction mixture was subsequently concentrated under reduced pressure (5 kPa) at a temperature in the region of 50° C
  3. dissolutionThe residue was dissolved in 30 cm3 of distilled water
  4. washthe aqueous phase was washed with 15 cm3 of dichloromethane
  5. extractionfinally, extracted with 3 times 20 cm3 of dichloromethane
  6. washwashed with 2 times 20 cm3 of distilled water
  7. dry with materialdried over magnesium sulfate
  8. filtrationAfter filtering
  9. concentrationconcentrating under reduced pressure (5 kPa) at a temperature in the region of 45° C.

Sources & evidence

ORD record
ord-2900dff4cffb45b6a94367ae7ade8789
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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