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

HRID 5502
Notes
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Reaction equation

HRID 5502 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6342
Acetonitrile
Solvent

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-7c6e013327b6432ebdbce4d8fc732f65
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05244899

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes