Water → HCID 11387473, compound

HRID 2186335Notes

Reaction equation

HRID 2186335 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[C:8]1([CH2:14][CH2:15][CH3:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH2:9]1.Cl.[CH3:18][O:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[N:26]=[CH:25][CH:24]=[C:23]2[CH2:30][CH2:31][CH2:32][C@@H:33]1[CH2:38][CH2:37][NH:36][CH2:35][C@@H:34]1[C:39]([OH:41])=[O:40].O>CN(C)C=O>[CH3:18][O:19][C:20]1[CH:21]=[C:22]2[C:27](=[CH:28][CH:29]=1)[N:26]=[CH:25][CH:24]=[C:23]2[CH2:30][CH2:31][CH2:32][C@@H:33]1[CH2:38][CH2:37][N:36]([CH2:16][CH2:15][CH2:14][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:35][C@@H:34]1[C:39]([O:41][CH2:16][CH2:15][CH2:14][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:40]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67321449HCID 67321449, compoundHCID 70174515HCID 70174515, compound

Product 1

HCID 11387473HCID 11387473, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.75 g of potassium carbonate and then 1.15 cm3 of 1-bromophenylpropane were added with stirring, at a temperature in the region of 25° C., to a solution of 0.91 g of (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]piperidine-3-carboxylic acid hydrochloride in 20 cm3 of anhydrous dimethylformamide. The suspension was brought to a temperature in the region of 60° C. for 17 hours. After cooling, the mixture was poured onto 200 cm3 of water and extracted with 3 times 30 cm3 of ether. The combined ethereal extracts were washed with 2 times 20 cm3 of water. The ethereal solution was extracted with 20 cm3 of normal aqueous hydrochloric acid and twice with 20 cm3 of water. The combined aqueous extracts were rendered alkaline by addition of solid sodium hydrogencarbonate. After extracting with 3 times 20 cm3 of ether and washing the ethereal extracts with 3 times 20 cm3 of water, drying was carried out over magnesium sulfate in the presence of 0.1 g of animal charcoal. After filtering through paper and then concentrating under reduced pressure (5 kPa) at a temperature in the region of 30° C, 0.84 g of 3-phenylpropyl (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-1-(3-phenylpropyl)piperidine-3-carboxylate was obtained in the form of an oil with a light brown color.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with 3 times 30 cm3 of ether
  3. washThe combined ethereal extracts were washed with 2 times 20 cm3 of water
  4. extractionThe ethereal solution was extracted with 20 cm3 of normal aqueous hydrochloric acid and twice with 20 cm3 of water
  5. additionby addition of solid sodium hydrogencarbonate
  6. extractionAfter extracting with 3 times 20 cm3 of ether
  7. washwashing the ethereal extracts with 3 times 20 cm3 of water
  8. customdrying
  9. filtrationAfter filtering through paper
  10. concentrationconcentrating under reduced pressure (5 kPa) at a temperature in the region of 30° C

Sources & evidence

ORD record
ord-1c9a47d749c3479a9e66e7a8ed18e4cb
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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