Tetrahydrofuran → HCID 9841264, compound

HRID 1032948Notes

Reaction equation

HRID 1032948 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][O:23][CH3:24])=[C:17]([N:25]([CH3:27])[CH3:26])[CH:16]=2)[O:9][CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])=[CH:4][CH:3]=1.O1CCCC1.C(=O)([O-])O.[Na+]>Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][O:23][CH3:24])=[C:17]([N:25]([CH3:26])[CH3:27])[CH:16]=2)[OH:9])=[CH:6][CH:7]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([N:25]([CH3:27])[CH3:26])[CH:16]=2)[O:9][CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 190269862-[1-(4-chlorophenyl)-1-(3-dimethylamino-4-methoxymethoxyphenyl)methoxy]-N,N-dimethylethanamine

Product 2

HCID 9841264HCID 9841264, compoundHCID 190269591-(4-Chlorophenyl)-1-(3-dimethylamino-4-methoxymethoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

A solution of the compound (2) (0.43 g, 1.09 mmol) obtained above in 1N hydrochloric acid (3.28 ml) and tetrahydrofuran (2 ml) was heated under reflux for 3 hours. Thereto was added additional 1N hydrochloric acid (2.18 ml) and the mixture was further heated for 1.5 hours. The reaction mixture was poured into a saturated aqueous solution of sodium hydrogencarbonate, extracted with methylene chloride, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel to give the title compound (Compound 1). Yield 0.15 g (39%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperaturethe mixture was further heated for 1.5 hours
  4. extractionextracted with methylene chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9338b6e3b521439b98db916fc2cc591e
Source dataset
uspto-grants-1994_05
Patent number
US05308840

Reaction notes

Loading…