Hydrochloric Acid → HCID 12542616, compound

HRID 1733328Notes

Reaction equation

HRID 1733328 reaction equation
[CH:1]([N:3]1[CH2:8][CH2:7][C:6]([O:22][CH3:23])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:5][CH2:4]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>CCOCC>[CH3:1][N:3]1[CH2:4][CH2:5][C:6]([O:22][CH3:23])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 12542615HCID 12542615, compound2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 12542616HCID 12542616, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a stirred mixture of 4.0 g of 1-formyl-4-methoxy-4-(α-phenyl-2-tolyl)piperidine, of Example 50b, in 300 ml of anhydrous ether, 0.68 g of 95% lithium aluminum hydride and 100 ml of anhydrous ether is added dropwise the solution of 1-formyl-4-methoxy-4-(α-phenyl-2-tolyl)piperidine, followed by stirring 16 hours at room temperature. The resultant mixture is quenched under N2 with distilled water. The mixture is gravity filtered, the phases are separated and the aqueous phase is further extracted with ether. The combined organic phase is dried (K2CO3), filtered and evaporated to give an oil. The oil is dissolved in ether, cooled and acidified with ethereal HCl. After 15 minutes of stirring, a crystalline precipitate is collected by suction filtration and dried in vacuo at 40° C. Recrystallization of the filter cake from absolute ethanol affords colorless crystals, mp 238°-239° C. of 1-methyl-4-methoxy-4-(α-phenyl-2-tolyl)piperidine.

Workup

  1. customThe resultant mixture is quenched under N2 with distilled water
  2. filtrationfiltered
  3. customthe phases are separated
  4. extractionthe aqueous phase is further extracted with ether
  5. dry with materialThe combined organic phase is dried (K2CO3)
  6. filtrationfiltered
  7. customevaporated
  8. customto give an oil
  9. temperaturecooled
  10. stirringAfter 15 minutes of stirring
  11. filtrationa crystalline precipitate is collected by suction filtration
  12. customdried in vacuo at 40° C
  13. customRecrystallization of the filter cake from absolute ethanol

Sources & evidence

ORD record
ord-242cd8404eca42f4af1cae42690f4b56
Source dataset
uspto-grants-1980_12
Patent number
US04241071

Reaction notes

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