Water → HCID 70098053, compound

HRID 2186360Notes

Reaction equation

HRID 2186360 reaction equation
S(Cl)([Cl:3])=O.C(O)(=O)C(O)=O.O[CH2:12][C@@H:13]1[C@H:18]([CH2:19][CH2:20][CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[C:29]([O:32][CH3:33])[CH:30]=3)[N:25]=[CH:24][CH:23]=2)[CH2:17][CH2:16][N:15]([CH2:34][CH2:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:14]1.O>C(Cl)(Cl)Cl>[Cl:3][CH2:12][C@@H:13]1[C@H:18]([CH2:19][CH2:20][CH2:21][C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[C:29]([O:32][CH3:33])[CH:30]=3)[N:25]=[CH:24][CH:23]=2)[CH2:17][CH2:16][N:15]([CH2:34][CH2:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 70175706HCID 70175706, compound

Product 1

HCID 70098053HCID 70098053, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

3.6 cm3 of thionyl chloride were added dropwise, at a temperature in the region of 20° C., to a stirred solution of 2.9 g of (3R,4R)-3-hydroxymethyl4-[3-(6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine oxalate in 20 cm3 of chloroform. The mixture was heated for 2 hours at a temperature in the region of 60° C. and then, after cooling, was poured onto 50 cm3 of water to which 250 g of ice had been added. After separating by settling from the chloroform phase, the mixture was extracted with 100 cm3 of dichloromethane. 5 g of sodium hydrogencarbonate were added to the aqueous phase, which was then extracted with 2 times 200 cm3 of dichloromethane. The organic extracts were dried over magnesium sulfate, filtered, and then evaporated under reduced pressure (5 kPa) at a temperature in the region of 40°. 1.3 g of (3R,4R)-3-chloromethyl-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine were obtained in the form of an oil with a brown color.

Workup

  1. temperatureafter cooling
  2. additionhad been added
  3. customAfter separating
  4. extractionthe mixture was extracted with 100 cm3 of dichloromethane
  5. addition5 g of sodium hydrogencarbonate were added to the aqueous phase, which
  6. extractionwas then extracted with 2 times 200 cm3 of dichloromethane
  7. dry with materialThe organic extracts were dried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure (5 kPa) at a temperature in the region of 40°

Sources & evidence

ORD record
ord-f9f5c37bdd37460dbc0844bb9362bb0e
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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