Triethylamine → HCID 53665275, compound

HRID 1252784Notes

Reaction equation

HRID 1252784 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Cl.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:17][O:18][C:19]1[CH:20]=[C:21]([C:25]([C:34]2([OH:40])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)=[CH:26][CH2:27][N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:22]=[CH:23][CH:24]=1.C(N(CC)CC)C>CN(C=O)C>[CH3:17][O:18][C:19]1[CH:20]=[C:21]([C:25]([C:34]2([OH:40])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39]2)=[CH:26][CH2:27][N:28]2[CH2:29][CH2:30][N:31]([CH2:6][C:5]3[CH:8]=[CH:9][CH:10]=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:32][CH2:33]2)[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10796Cesium carbonateHCID 699943-Methoxybenzyl chlorideHCID 53653102HCID 53653102, compound

Product 1

HCID 53665275HCID 53665275, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Methoxybenzyl chloride (1.28 g, 7.5 mol) and Cs2CO3 (5.9 g, 18 mmole) were added to a solution of 1-[1-(3-methoxyphenyl)-3-(1-piperazinyl)-1-propenyl]cyclohexanol (2.0 g, 6 mmole) in DMF (50 mL) and the mixture stirred at room temperature for one hour. Triethylamine (0.25 mL) was then added and the reaction mixture stirred overnight. The solvent was evaporated and the residue dissolved in chloroform. The solution was washed with water and the water back-extracted with chloroform. The combined organic solution was washed with brine, dried over magnesium sulfate and evaporated. The product was purified using column chromatography with chloroform as eluent and the purified title compound was converted to the hydrochloride. Yield 530 mg, m.p. 169°-171° C.

Workup

  1. stirringthe reaction mixture stirred overnight
  2. customThe solvent was evaporated
  3. dissolutionthe residue dissolved in chloroform
  4. washThe solution was washed with water
  5. extractionthe water back-extracted with chloroform
  6. washThe combined organic solution was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customThe product was purified
  10. customthe purified title compound

Sources & evidence

ORD record
ord-41052dc3995240838f0a4fbfebab37c1
Source dataset
uspto-grants-1988_05
Patent number
US04745191

Reaction notes

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