Water → HCID 70177231, compound

HRID 2186359Notes

Reaction equation

HRID 2186359 reaction equation
[C-:1]#[N:2].[Na+].Cl[CH2:5][C@@H:6]1[C@H:11]([CH2:12][CH2:13][CH2:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=3)[N:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9][N:8]([CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:7]1.O>CS(C)=O>[CH3:26][O:25][C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[N:18]=[CH:17][CH:16]=[C:15]2[CH2:14][CH2:13][CH2:12][C@@H:11]1[CH2:10][CH2:9][N:8]([CH2:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:7][C@@H:6]1[CH2:5][C:1]#[N:2]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 70098053HCID 70098053, compound

Product 1

HCID 70177231HCID 70177231, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

0.565 g of sodium cyanide was added to a stirred solution of 1.3 g of (3R,4R)-3-chloromethyl-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine in 50 cm3 of dimethyl sulfoxide and then the mixture was heated at a temperature in the region of 60° C. for 20 hours. After cooling, the reaction mixture was poured onto 500 cm3 of water and then extracted with 2 times 200 cm3 of diethyl ether. The combined extracts were dried over magnesium sulfate, filtered, and then evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The residue obtained was purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45 μm, diameter 2 cm; 32 g), elution was carried out with ethyl acetate, and 15-cm3 fractions were collected. Fractions 12 to 19 were combined and then evaporated (5 kPa) at a temperature in the region of 40° C. 0.34 g of (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-[3-phenylpropyl]piperidine-3-acetonitrile was obtained in the form of an oil with a yellow color.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with 2 times 200 cm3 of diethyl ether
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  6. customThe residue obtained
  7. customwas purified by chromatography at atmospheric pressure on a column of silica gel (particle size 20-45 μm, diameter 2 cm; 32 g), elution
  8. customwere collected
  9. customevaporated (5 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-f42f45f0595f4569b4ff893527c4ea9c
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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