Sodium Iodide → HCID 54246294, compound

HRID 1763481Notes

Reaction equation

HRID 1763481 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6].[CH3:13][C@H:14]1[CH2:19][CH2:18][CH2:17][C@@H:16]([CH3:20])[NH:15]1.[I-].[Na+]>>[CH3:13][C@H:14]1[CH2:19][CH2:18][CH2:17][C@@H:16]([CH3:20])[N:15]1[CH:4]([CH2:3][CH3:2])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6]

Participants

4

Reactant 3

HCID 5238Sodium IodideHCID 2535334-ChlorobutyrophenoneHCID 641768rel-(2R,6S)-2,6-Dimethylpiperidine

Product 1

HCID 54246294HCID 54246294, compound

Procedure

A mixture of 619 g. of γ-chlorobutyrophenone, ethylene ketal, 700 g. of cis-2,6-dimethylpiperidine and 16 g. of sodium iodide is stirred and heated at reflux for 48 hours. The mixture is cooled, diluted with 1 l. of anhydrous ether and filtered to remove cis-2,6-dimethylpiperidine hydrochloride. The filter cake is washed with 1 l. of ether and the filtrate and washings combined. The resulting ether solution is washed five times with 500 ml. portions of water, then extracted with a solution of 300 ml. of concentrated hydrochloric acid in 3 l. of water. The acid extract is washed with 500 ml. of ether, then heated to 70°-80° and allowed to cool to room temperature over a period of 16 hours. The resulting solution is basified with 50% aqueous sodium hydroxide and the organic layer is separated. The aqueous layer is extracted with 500 ml. of ether and the extract is combined with the organic layer. The combined extract is washed several times with water, dried and evaporated. The oily residue is distilled at reduced pressure to give cis-α-(2,6-dimethylpiperidino)butyrophenone; b.p. 138°-141° C./0.1 mm.

Workup

  1. additionA mixture of 619 g
  2. temperatureheated
  3. temperatureat reflux for 48 hours
  4. temperatureThe mixture is cooled
  5. additiondiluted with 1 l
  6. filtrationof anhydrous ether and filtered
  7. customto remove cis-2,6-dimethylpiperidine hydrochloride
  8. washThe filter cake is washed with 1 l
  9. washThe resulting ether solution is washed five times with 500 ml
  10. extractionportions of water, then extracted with a solution of 300 ml
  11. extractionThe acid extract
  12. washis washed with 500 ml
  13. temperatureof ether, then heated to 70°-80°
  14. customthe organic layer is separated
  15. extractionThe aqueous layer is extracted with 500 ml
  16. extractionThe combined extract
  17. washis washed several times with water
  18. customdried
  19. customevaporated
  20. distillationThe oily residue is distilled at reduced pressure

Sources & evidence

ORD record
ord-dc442d81238348c48d9c4f230a73d3af
Source dataset
uspto-grants-1978_09
Patent number
US04112103

Reaction notes

Loading…