Water → HCID 69354268, compound

HRID 2186337Notes

Reaction equation

HRID 2186337 reaction equation
C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][CH:14]=[C:13]2[CH2:20][CH2:21][CH2:22][C@@H:23]1[CH2:28][CH2:27][NH:26][CH2:25][C@@H:24]1[CH:29]=[CH2:30].[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.O>C(Cl)(Cl)Cl>[C:31]([N:26]1[CH2:27][CH2:28][C@@H:23]([CH2:22][CH2:21][CH2:20][C:13]2[C:12]3[C:17](=[CH:18][CH:19]=[C:10]([O:9][CH3:8])[CH:11]=3)[N:16]=[CH:15][CH:14]=2)[C@@H:24]([CH:29]=[CH2:30])[CH2:25]1)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 3050111Viqualine

Product 1

HCID 69354268HCID 69354268, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

18.4 cm3 of triethylamine were added to a stirred solution of 20.8 g of (3R,4R)-4-[3-(6-methoxyquinolin-4-yl)propyl]-3-vinylpiperidine in 270 cm3 of chloroform, followed, over 1 hour, by a solution of 7.2 cm3 of benzoyl chloride in 50 cm3 of chloroform. After stirring the mixture at a temperature in the region of 20° C. for 1 hour 30 minutes, 100 cm3 of distilled water were added to the reaction mixture. The chloroform phase was separated by settling, washed with 2 times 100 cm3 of water, and then dried over magnesium sulfate. After filtering through paper, the chloroform solution was concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C. 25 g of (3R,4R)-1-benzoyl-4-[3-(6-methoxyquinolin-4-yl)propyl]-3-vinylpiperidine were obtained in the form of a brown oil.

Workup

  1. additionwere added to the reaction mixture
  2. customThe chloroform phase was separated
  3. washwashed with 2 times 100 cm3 of water
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtering through paper
  6. concentrationthe chloroform solution was concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C

Sources & evidence

ORD record
ord-64d1c3be898f4faa845b25165e783e42
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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