Hydrochloric Acid → 1-(4-Dimethylamino-4-thiophen-2-yl-cyclohexyl)-2-phenylethanol

HRID 2063721Notes

Reaction equation

HRID 2063721 reaction equation
Cl.C(OC([O:7][CH:8]([CH:16]1[CH2:21][CH2:20][C:19]([N:27]([CH3:29])[CH3:28])([C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)[CH2:18][CH2:17]1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)C)C.[OH-].[Na+]>O1CCCC1.C(OCC)C>[CH3:29][N:27]([CH3:28])[C:19]1([C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)[CH2:18][CH2:17][CH:16]([CH:8]([OH:7])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:21][CH2:20]1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 66886988{4-[1-(1-Ethoxy-ethoxy)-2-phenylethyl]-1-thiophen-2-yl-cyclohexyl}dimethylamine

Product 1

HCID 442521071-(4-Dimethylamino-4-thiophen-2-yl-cyclohexyl)-2-phenylethanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

2 M hydrochloric acid (20 ml) was added to a solution of {4-[1-(1-ethoxy-ethoxy)-2-phenylethyl]-1-thiophen-2-yl-cyclohexyl}dimethylamine (1.10 g, 2.73 mmol) in tetrahydrofuran (20 ml) and the reaction mixture was stirred at room temperature overnight. It was then rendered alkaline with 4 M sodium hydroxide solution and extracted with methylene chloride (4×10 ml). The combined organic phases were dried with sodium sulfate and concentrated i. vac. The crude product (956 mg) was purified by flash chromatography with cyclohexane/ethyl acetate (3:2) and then methanol. The two product fractions obtained in this way were each taken up in diethyl ether, and 2 M hydrochloric acid (20 ml) was added. The phases were separated. The acid aqueous phases were extracted with diethyl ether (3×10 ml) and thereafter rendered alkaline with 4 M sodium hydroxide solution. The aqueous phases were extracted with methylene chloride (4×10 ml). The combined organic phases were dried with sodium sulfate and concentrated i. vac.

Workup

  1. extractionextracted with methylene chloride (4×10 ml)
  2. dry with materialThe combined organic phases were dried with sodium sulfate
  3. concentrationconcentrated i
  4. customThe crude product (956 mg) was purified by flash chromatography with cyclohexane/ethyl acetate (3:2)
  5. customThe two product fractions obtained in this way
  6. customThe phases were separated
  7. extractionThe acid aqueous phases were extracted with diethyl ether (3×10 ml)
  8. extractionThe aqueous phases were extracted with methylene chloride (4×10 ml)
  9. dry with materialThe combined organic phases were dried with sodium sulfate
  10. concentrationconcentrated i

Sources & evidence

ORD record
ord-d051e3010e9a419385704637be55670c
Source dataset
uspto-grants-2012_10
Patent number
US08288406B2

Reaction notes

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