Triethylamine → N-1-Azabicyclo[2.2.2]oct-3-yl-2-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]acetamide, monohydrochloride

HRID 2051551Notes

Reaction equation

HRID 2051551 reaction equation
Cl.[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([NH:10][C:11](=[O:14])[CH2:12][Cl:13])[CH2:3]2.[CH3:15][C:16]([C:19]1[CH:24]=[C:23]([SH:25])[CH:22]=[C:21]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]=1[OH:30])([CH3:18])[CH3:17].C(N(CC)CC)C>C(#N)C>[ClH:13].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH:4]([NH:10][C:11](=[O:14])[CH2:12][S:25][C:23]1[CH:22]=[C:21]([C:26]([CH3:27])([CH3:28])[CH3:29])[C:20]([OH:30])=[C:19]([C:16]([CH3:18])([CH3:17])[CH3:15])[CH:24]=1)[CH2:3]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 703702,6-Di-tert-butyl-4-mercaptophenolHCID 131716900N-1-Azabicyclo[2.2.2]oct-3-yl-2-chloroacetamide, monohydrochloride

Product 1

HCID 131716901N-1-Azabicyclo[2.2.2]oct-3-yl-2-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]acetamide, monohydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared by dissolving the product of Example 17 (2.0 g, 0.0084 mole) and 2,6-bis (1,1-dimethylethyl)-4-mercaptophenol (1.99 g, 0.0084 mole) in acetonitrile (25 ml). Triethylamine (5 ml) was added to the mixture and the mixture stirred at room temperature for 12 hours then refluxed for 72 hours. The hot mixture was filtered and the solvent removed on a rotary evaporator. The residue was triturated with hexane and dissolved in hot ethyl acetate and allowed to cool. After filtering, the solvent was removed by a rotary evaporator and the residue recrystallized from ethyl acetate-methanol-ethyl ether to give a tan solid. The structure was confirmed by mass spectroscopy M+ 404.

Workup

  1. temperaturethen refluxed for 72 hours
  2. filtrationThe hot mixture was filtered
  3. customthe solvent removed on a rotary evaporator
  4. customThe residue was triturated with hexane
  5. dissolutiondissolved in hot ethyl acetate
  6. temperatureto cool
  7. filtrationAfter filtering
  8. customthe solvent was removed by a rotary evaporator
  9. customthe residue recrystallized from ethyl acetate-methanol-ethyl ether
  10. customto give a tan solid

Sources & evidence

ORD record
ord-9fdec6901e714520a4f2c4ea7904e45e
Source dataset
uspto-grants-1991_05
Patent number
US05019597

Reaction notes

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