Hydrochloric Acid → HCID 11793231, compound

HRID 1722736Notes

Reaction equation

HRID 1722736 reaction equation
[H-].[Na+].C1(C)C(S)=CC=CC=1.[CH3:11][O:12][C:13]1[CH:14]=[C:15]([CH:30]=[C:31]([O:35][CH3:36])[C:32]=1[O:33]C)[CH2:16][O:17][CH2:18][C:19]([N:27]([CH3:29])[CH3:28])([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)[CH2:20][CH3:21].Cl>C1(C)C=CC=CC=1.CN(C)P(=O)(N(C)C)N(C)C>[OH:33][C:32]1[C:31]([O:35][CH3:36])=[CH:30][C:15]([CH2:16][O:17][CH2:18][C:19]([N:27]([CH3:28])[CH3:29])([C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)[CH2:20][CH3:21])=[CH:14][C:13]=1[O:12][CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 87122-ThiocresolHCID 24758Sodium hydrideHCID 10523782HCID 10523782, compound

Product 1

HCID 11793231HCID 11793231, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 12679HexamethylphosphoramideSolvent

Procedure

Sodium hydride (63.5% oil dispersion, 0.66 g) is added to a solution of thiocresol (2.2 g) in toluene (40 ml) under ice-cooling and the mixture is stirred at room temperature for 30 minutes. A solution of 1-(3,4,5-trimethoxybenzyloxymethyl)-1-(2-thienyl)-N,N-dimethylpropylamine (2.2 g) in toluene (20 ml) is added to the mixture under ice-cooling and hexamethylphosphoric triamide (3 ml) is added thereto. The mixture is refluxed in nitrogen atmosphere for 5 hours. After cooling, 10% hydrochloric acid is added to the mixture and the aqueous layer is collected therefrom. The aqueous layer is washed with ether and adjusted to pH 8 with sodium bicarbonate and then extracted with ether. The extract is dried and concentrated under reduced pressure to remove solvent. The residue is purified by silica gel column chromatography (solvent, chloroform:ethanol=100:1). The resulting product is recrystallized from a mixture of ethyl acetate and n-hexane, whereby 1-(4-hydroxy-3,5- dimethoxybenzyloxymethyl)-1-(2-thienyl)-N,N-dimethylpropylamine (2 g) is obtained as colorless pillars.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. temperatureThe mixture is refluxed in nitrogen atmosphere for 5 hours
  4. temperatureAfter cooling
  5. customthe aqueous layer is collected
  6. washThe aqueous layer is washed with ether
  7. extractionextracted with ether
  8. customThe extract is dried
  9. concentrationconcentrated under reduced pressure
  10. customto remove solvent
  11. customThe residue is purified by silica gel column chromatography (solvent, chloroform:ethanol=100:1)
  12. customThe resulting product is recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-9a69a17ea35f4613858f45c8f9370575
Source dataset
uspto-grants-1989_08
Patent number
US04857543

Reaction notes

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