Potassium Hydroxide → HCID 19010885, compound

HRID 1741776Notes

Reaction equation

HRID 1741776 reaction equation
[C:1]1([C:7]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][NH:11][C:10](=[O:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].[CH3:22][N:23]([CH3:28])[CH2:24][CH2:25][CH2:26][Cl:27]>CS(C)=O>[ClH:27].[CH3:22][N:23]([CH3:28])[CH2:24][CH2:25][CH2:26][N:11]1[CH2:12][C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][C:10]1=[O:13]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 19010883HCID 19010883, compound

Product 1

HCID 19010885HCID 19010885, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a vigorously stirred mixture of 5,5-diphenyl 2-piperidinone (5.0 g) and 45% potassium hydroxide (15 ml) in dimethyl sulfoxide (50 ml) was added in one portion 3-(dimethylamino)propyl chloride (5.5g) at room temperature. The reaction was stirred overnight, then it was partitioned between water and ethyl acetate. The organic layer was separated, washed with water and dried. Evaporation of the solvents afforded a syrup which was chromatographed over ammonia-washed silica gel and the resultant title product amine was treated with isopropanol/HCl. The precipitated .hydrochloride salt was collected by filtration, recrystallized from absolute ethanol and dried to give the title product as the hydrochloride salt (3.6 g), mp 220°-5° C.

Workup

  1. customit was partitioned between water and ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water
  4. customdried
  5. customEvaporation of the solvents
  6. customafforded a syrup which
  7. customwas chromatographed over ammonia-
  8. washwashed silica gel
  9. additionthe resultant title product amine was treated with isopropanol/HCl
  10. filtrationhydrochloride salt was collected by filtration
  11. customrecrystallized from absolute ethanol
  12. customdried

Sources & evidence

ORD record
ord-7c5c7ee8d4d3457fbbb71a78b2f08c83
Source dataset
uspto-grants-1994_08
Patent number
US05334720

Reaction notes

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