Triethylamine → HCID 10572652, compound

HRID 1722732Notes

Reaction equation

HRID 1722732 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)([CH2:6][CH3:7])[CH2:4][OH:5].C(N(CC)CC)C.CN(C1C=CC=CN=1)C.[CH3:30][O:31][C:32]1[CH:33]=[C:34]([CH:38]=[C:39]([O:43][CH3:44])[C:40]=1[O:41][CH3:42])[C:35](Cl)=[O:36]>O1CCCC1>[CH3:44][O:43][C:39]1[CH:38]=[C:34]([CH:33]=[C:32]([O:31][CH3:30])[C:40]=1[O:41][CH3:42])[C:35]([O:5][CH2:4][C:3]([N:2]([CH3:1])[CH3:13])([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[CH2:6][CH3:7])=[O:36]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 10512214HCID 10512214, compound

Product 1

HCID 10572652HCID 10572652, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Dimethylamino-2-(2-thienyl)-1-butanol (8 g), triethylamine (4.85 g) and dimethylaminopyridine (catalytic amount) are dissolved in tetrahydrofuran (10 ml), and 3,4,5-trimethoxybenzoyl chloride (11.1 g) is gradually added to the solution under ice-cooling. The mixture is stirred at room temperature for 16 hours and concentrated under reduced pressure to remove solvent. The residue is dissolved in diluted hydrochloric acid, and the solution is washed with ether. The solution is alkalized with potassium carbonate and extracted with ethyl acetate. The extract is washed with an aqueous saturated sodium chloride solution, dried and then concentrated under reduced pressure to remove solvent. The residue is purified by silica gel column chromatography (solvent, n-hexane:ethyl acetate=5:2), whereby 2-dimethylamino-2-(2-thienyl)-butyl 3,4,5-trimethoxybenzoate (12.8 g) is obtained as colorless oil.

Workup

  1. temperaturecooling
  2. concentrationconcentrated under reduced pressure
  3. customto remove solvent
  4. dissolutionThe residue is dissolved in diluted hydrochloric acid
  5. washthe solution is washed with ether
  6. extractionextracted with ethyl acetate
  7. washThe extract is washed with an aqueous saturated sodium chloride solution
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. customto remove solvent
  11. customThe residue is purified by silica gel column chromatography (solvent, n-hexane:ethyl acetate=5:2)

Sources & evidence

ORD record
ord-130b8aab22ff4c91b987f0b5af577933
Source dataset
uspto-grants-1989_08
Patent number
US04857543

Reaction notes

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