Hydrochloric Acid → N-[1-(phenylmethyl)4-methyl-4-piperidinyl]acetamide hydrochloride

HRID 2294211Notes

Reaction equation

HRID 2294211 reaction equation
[CH3:1][C:2]1(O)[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.S(=O)(=O)(O)O.C(=O)([O-])[O-:22].[K+].[K+].[OH-].[K+].[ClH:29].[C:30](#[N:32])[CH3:31]>>[ClH:29].[C:9]1([CH2:8][N:5]2[CH2:6][CH2:7][C:2]([NH:32][C:30](=[O:22])[CH3:31])([CH3:1])[CH2:3][CH2:4]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 108459131-Benzyl-4-methylpiperidin-4-ol

Product 1

HCID 21472468N-[1-(phenylmethyl)4-methyl-4-piperidinyl]acetamide hydrochloride

Procedure

To a stirred and hot (60°-70° C.) mixture of 36 g of 4-methyl-1-(phenylmethyl)-4-piperidinol and 15 ml of acetonitrile were added dropwise 55 ml of concentrated sulfuric acid while cooling. After complete addition, stirring was continued for 20 hours at room temperature. The reaction mixture was poured on crushed ice. The whole was neutralized with potassium carbonate and then strongly alkalinized with a potassium hydroxide solution 15%. The free base was extracted with ethyl acetate. The aqueous phase was saturated with potassium hydroxide and extracted again with ethyl acetate. The combined extracts were dried, filtered and evaporated The semi-solid residue was triturated in 1,1'-oxybisethane and filtered. To the filtrate was added 2-propanone until a clear solution was obtained. Then gaseous hydrogen chloride was introduced into it. The precipitated solid salt was filtered off and recrystallized from 2-propanol, yielding 21.5 g of N-[1-(phenylmethyl)-4-methyl-4-piperidinyl]acetamide hydrochloride; mp. 288°-289° C. (interm. 4).

Workup

  1. temperaturewhile cooling
  2. additionAfter complete addition
  3. stirringstirring
  4. additionThe reaction mixture was poured
  5. customon crushed ice
  6. extractionThe free base was extracted with ethyl acetate
  7. extractionextracted again with ethyl acetate
  8. customThe combined extracts were dried
  9. filtrationfiltered
  10. customevaporated The semi-solid residue
  11. customwas triturated in 1,1'-oxybisethane
  12. filtrationfiltered
  13. additionTo the filtrate was added 2-propanone until a clear solution
  14. customwas obtained
  15. filtrationThe precipitated solid salt was filtered off
  16. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-f724d8baff1f43738f53d385bf519352
Source dataset
uspto-grants-1997_11
Patent number
US05688814

Reaction notes

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