Hydrochloric Acid → 1-(4-Dimethylamino-4-phenylcyclohexyl)-2-phenoxyethanol

HRID 2063743Notes

Reaction equation

HRID 2063743 reaction equation
Cl.C(OC([O:7][CH:8]([CH:17]1[CH2:22][CH2:21][C:20]([N:29]([CH3:31])[CH3:30])([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:19][CH2:18]1)[CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C)C.[OH-].[Na+]>CC(C)=O>[CH3:30][N:29]([CH3:31])[C:20]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:21][CH2:22][CH:17]([CH:8]([OH:7])[CH2:9][O:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:18][CH2:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66886952{4-[1-(1-Ethoxy-ethoxy)-2-phenoxyethyl]-1-phenylcyclohexyl}dimethylamine

Product 1

HCID 442519591-(4-Dimethylamino-4-phenylcyclohexyl)-2-phenoxyethanol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2 M hydrochloric acid (10 ml) was added to a solution of {4-[1-(1-ethoxy-ethoxy)-2-phenoxyethyl]-1-phenylcyclohexyl}dimethylamine (892 mg, 2.16 mmol) in acetone (30 ml) and the mixture was stirred at room temperature overnight. The pH of the mixture was then rendered alkaline with 0.5 M sodium hydroxide solution and the mixture was subsequently extracted with methylene chloride (3×30 ml). The combined organic phases were dried with sodium sulfate and concentrated in vacuo. The crude product (1.26 g) was purified by flash chromatography with ethyl acetate/methanol (9:1→0:1).

Workup

  1. extractionthe mixture was subsequently extracted with methylene chloride (3×30 ml)
  2. dry with materialThe combined organic phases were dried with sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product (1.26 g) was purified by flash chromatography with ethyl acetate/methanol (9:1→0:1)

Sources & evidence

ORD record
ord-080fccc17faa49e79b0c963ca6ecc1db
Source dataset
uspto-grants-2012_10
Patent number
US08288406B2

Reaction notes

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