Hydrochloric Acid → HCID 21250998, compound

HRID 1531842Notes

Reaction equation

HRID 1531842 reaction equation
Cl.C[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[O:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][CH2:18]1>C(O)(C)C.ClCCl>[OH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[O:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 21251019HCID 21251019, compound

Product 1

HCID 21250998HCID 21250998, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

2.7 ml of a solution of hydrochloric acid (0.5 N) in isopropanol are slowly added, at 0° C. to a solution of 0.5 g (1.32 mmol) of 1-(2-methoxyphenyl)-2-[[1-(phenylmethyl)piperidin-4-yl]methoxy]-1H-imidazole in 15 ml of dichloromethane. The solvents are removed by evaporation and then the product is taken up in 15 ml of dichloromethane. The solution is cooled to −15° C. and 1.05 ml of boron tribromide is slowly added. The reaction medium is stirred for 3 h 30 min while allowing the temperature to return to 20° C. The reaction mixture is poured over ice and sodium bicarbonate is added until a pH=8 is obtained. After separating upon settling out, the aqueous phase is extracted twice with ethyl acetate and the combined organic phases are washed with water and then with brine. The medium is dried over magnesium sulphate, filtered and concentrated. The expected compound is purified on a silica gel, eluting with a 99:1 to 93:7 CH2Cl2/CH3OH mixture. 0.355 g of product is obtained. (Yield 74%)

Workup

  1. customThe solvents are removed by evaporation
  2. addition1.05 ml of boron tribromide is slowly added
  3. customto return to 20° C
  4. additionThe reaction mixture is poured over ice and sodium bicarbonate
  5. additionis added until a pH=8
  6. customis obtained
  7. customAfter separating
  8. extractionthe aqueous phase is extracted twice with ethyl acetate
  9. washthe combined organic phases are washed with water
  10. dry with materialThe medium is dried over magnesium sulphate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe expected compound is purified on a silica gel
  14. washeluting with a 99:1 to 93:7 CH2Cl2/CH3OH mixture

Sources & evidence

ORD record
ord-8fef19920a5a4616b1316765ed22f350
Source dataset
uspto-grants-2001_03
Patent number
US06200991B1

Reaction notes

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