Pyridine → 4-(3-Phenylpropyl)piperidine-1-carbonyl chloride

HRID 1576755Notes

Reaction equation

HRID 1576755 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[C:5]1([CH2:11][CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.N1C=CC=CC=1>C1(C)C=CC=CC=1>[C:5]1([CH2:11][CH2:12][CH2:13][CH:14]2[CH2:15][CH2:16][N:17]([C:1]([Cl:4])=[O:2])[CH2:18][CH2:19]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6371PhosgeneHCID 876784-(3-Phenylpropyl)piperidine

Product 1

HCID 227508054-(3-Phenylpropyl)piperidine-1-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Phosgene is passed into 150 ml. of dry toluene at 0°C. until 17 g. of gas has been absorbed. The cooling bath is removed, and to the phosgene solution is added, dropwise, with stirring, during 1 hour, a solution prepared from 27.6. g. of 4-(3-phenylpropyl)piperidine, and 12.3 ml. of pyridine and 100 ml. of toluene. After the end of the addition, the reaction mixture is stored at ambient temperature for 16 hours. At this point, the reaction mixture is filtered, and the filtrate is evaporated in vacuo, leaving 39 g. of the title compound in crude state. The product is contaminated with toluene, but it is sufficiently pure for coupling with alkenesulfonamides.

Workup

  1. customat 0°C.
  2. customof gas has been absorbed
  3. customThe cooling bath is removed
  4. additionto the phosgene solution is added
  5. customa solution prepared from 27.6
  6. additionAfter the end of the addition
  7. waitthe reaction mixture is stored at ambient temperature for 16 hours
  8. filtrationAt this point, the reaction mixture is filtered
  9. customthe filtrate is evaporated in vacuo
  10. customleaving 39 g

Sources & evidence

ORD record
ord-e6608902525045789677b803119203a3
Source dataset
uspto-grants-1976_09
Patent number
US03983107

Reaction notes

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