Methanol → HCID 21545537, compound

HRID 1605901Notes

Reaction equation

HRID 1605901 reaction equation
[C:1]([C:4]1[CH:28]=[CH:27][CH:26]=[CH:25][C:5]=1[O:6][CH2:7][CH:8]([OH:24])[CH2:9][N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])[CH2:12][CH2:11]1)([OH:3])=[O:2].S(=O)(=O)(O)O.[CH3:34]O>>[CH3:34][O:2][C:1]([C:4]1[CH:28]=[CH:27][CH:26]=[CH:25][C:5]=1[O:6][CH2:7][CH:8]([OH:24])[CH2:9][N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])[CH2:12][CH2:11]1)=[O:3]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 21545547HCID 21545547, compound

Product 1

HCID 21545537HCID 21545537, compound

Procedure

A solution of crude 1-(2-carboxyphenoxy)-3-[4-(2-methoxyphenyl)piperazin-1-yl]propan-2-ol (43 g.) in 250 ml. of methanol containing 25 ml. of concentrated sulfuric acid was refluxed for 1.5 hours and then allowed to cool to room temperature. Upon completion of this step, the resulting solution was concentrated in vacuo to a volume of approximately 100 ml., then poured into 250 ml. of water and made alkaline with aqueous sodium hydroxide solution. The latter basified solution was next thoroughly extracted with chloroform, and the chloroform extracts subsequently combined and dried over anhydrous magnesium sulfate. After removal of the drying agent by means of filtration and the solvent by means of evaporation under reduced pressure, there were ultimately obtained 34 g. of crude product as residual material. Crystallization of a portion of the latter material from methanol then gave pure 1-(2-methoxycarbonylphenoxy)-3-[4-(2-methoxyphenyl)piperazin-1-yl]propan-2-ol, m.p. 127°-128°C.

Workup

  1. concentrationUpon completion of this step, the resulting solution was concentrated in vacuo to a volume of approximately 100 ml
  2. addition, then poured into 250 ml
  3. extractionnext thoroughly extracted with chloroform
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removal of the drying agent
  6. filtrationby means of filtration
  7. customthe solvent by means of evaporation under reduced pressure, there
  8. customCrystallization of a portion of the latter material from methanol

Sources & evidence

ORD record
ord-c63b42f74ba4410b9152361f8d853b7b
Source dataset
uspto-grants-1976_04
Patent number
US03951983

Reaction notes

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