Potassium Iodide → 4-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-2,2-dimethylphenethyl acetate

HRID 263732

Reaction equation

HRID 263732 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:18])[CH2:14][CH2:15][CH2:16]Cl)=[CH:9][C:8]1([CH3:20])[CH3:19])(=[O:3])[CH3:2].[C:21]1([C:27]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[OH:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])O.[K+].[I-].[K+]>O.C1(C)C=CC=CC=1>[C:1]([O:4][CH2:5][CH2:6][CH:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:18])[CH2:14][CH2:15][CH2:16][N:32]2[CH2:33][CH2:34][CH:29]([C:27]([OH:28])([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:30][CH2:31]2)=[CH:9][C:8]1([CH3:20])[CH3:19])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 15723AzacyclonolHCID 516893Potassium BicarbonateHCID 229063004-(4-Chloro-1-oxobutyl)-2,2-dimethylphenethyl acetate

Product 1

HCID 229063064-[4-[4-(Hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-2,2-dimethylphenethyl acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent2×

Procedure

Mix 4-(4-chloro-1-oxobutyl)-2,2-dimethylphenethyl acetate (99.5 g, 0.335 mol), α,α-diphenyl-4-piperidinemethanol (101.8 g, 0.335 mol), potassium hydrogen carbonate (83.8 g, 0.838 mol), potassium iodide (1.00 g, 0.006 mol), toluene (600 mL) and water (220 mL). Stir at reflux for 72 hours, add toluene (200 mL) and deionized water (100 mL). Filter through filter aid while at 80° C. and separate the organic phase. Dry (MgSO4), filter and purify by chromatography (ethyl acetate) to give 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-2,2-dimethylphenethyl acetate as an oily solid.

Workup

  1. temperatureat reflux for 72 hours
  2. filtrationFilter
  3. filtrationthrough filter aid while at 80° C.
  4. customseparate the organic phase
  5. dry with materialDry (MgSO4)
  6. filtrationfilter
  7. custompurify by chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-c008f4bf3bed4e39a50ab9e5458ce682
Source dataset
uspto-grants-1997_07
Patent number
US05644061

Linked notes

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