Potassium Iodide → cis-4-(benzoylamino)-3-methoxy-N,N-dimethyl-alpha,alpha-diphenyl-1-piperidinebutanamide

HRID 846792Notes

Reaction equation

HRID 846792 reaction equation
[Br-].[C:2]1([C:8]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11][O:10][C:9]2=[N+:13]([CH3:15])[CH3:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][O:23][C@H:24]1[C@@H:29]([NH:30][C:31](=[O:38])[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:28][CH2:27][NH:26][CH2:25]1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>O.CC(C)CC(=O)C>[C:31]([NH:30][C@H:29]1[CH2:28][CH2:27][N:26]([CH2:11][CH2:12][C:8]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]([N:13]([CH3:15])[CH3:14])=[O:10])[CH2:25][C@H:24]1[O:23][CH3:22])(=[O:38])[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 2723589(Dihydro-3,3-diphenyl-3H-furan-2-ylidene)dimethylammonium bromideHCID 15096867cis-N-(3-methoxy-4-piperidinyl)benzamide

Product 1

HCID 15096783cis-4-(benzoylamino)-3-methoxy-N,N-dimethyl-alpha,alpha-diphenyl-1-piperidinebutanamideYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 7.6 parts of N-(dihydro-3,3-diphenyl-2(3H)-furanylidene)-N-methylmethanaminium bromide, 4.7 parts of cis-N-(3-methoxy-4-piperidinyl)benzamide, 3.8 parts of sodium carbonate, 0.1 parts of potassium iodide and 240 parts of 4-methyl-2-pentanone was stirred and refluxed for 18 hours using a water-separator. The reaction mixture was cooled to room temperature and washed with water. The organic phase was separated, dried, filtered and evaporated. The oily residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 3.5 parts (35%) of cis-4-(benzoylamino)-3-methoxy-N,N-dimethyl-α,α-diphenyl-1-piperidinebutanamide; mp. 146.6° C. (compound 122).

Workup

  1. temperaturerefluxed for 18 hours
  2. washwashed with water
  3. customThe organic phase was separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe oily residue was purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  9. customThe pure fractions were collected
  10. customthe eluent was evaporated
  11. customThe residue was crystallized from 2,2'-oxybispropane
  12. filtrationThe product was filtered off
  13. customdried

Sources & evidence

ORD record
ord-8ef23e35b02644b1b19e48395c346535
Source dataset
uspto-grants-1992_08
Patent number
US05137896

Reaction notes

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