Water → Meptazinol

HRID 2049324Notes

Reaction equation

HRID 2049324 reaction equation
[CH2:1]([C:3]1([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([CH3:10])[C:4]1=O)[CH3:2].[H-].[Li+].[Al+3].[H-].[H-].[H-].O>O1CCCC1>[CH2:1]([C:3]1([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([CH3:10])[CH2:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 27945733-Ethylhexahydro-3-(3-hydroxyphenyl)-1-methyl-2H-azepin-2-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 41049MeptazinolYield 64.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-ethylhexahydro-3-(3-hydroxyphenyl)-1-methyl-2H-azepin-2-one (1.5 g) in dry tetrahydrofuran was added to a stirred suspension of aluminium lithium hydride (0.48 g) and heated under reflux for 5 hours. The reaction mixture was cooled and decomposed by the addition of water and the precipitate filtered. The precipitate was washed with tetrahydrofuran and the combined filtrate and washings evaporated to a solid. The solid was dissolved in water and ammonium chloride added. The precipitated oil was extracted with dichloromethane, dried over anhydrous magnesium sulphate and evaporated to leave a solid which was recrystallised from acetonitrile to give 0.91 g of the title compound, m.p. 127.5°-133° C., identical with material prepared by an alternative route described in U.K. specification No. 1,285,025.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. temperatureThe reaction mixture was cooled
  4. filtrationthe precipitate filtered
  5. washThe precipitate was washed with tetrahydrofuran
  6. customthe combined filtrate and washings evaporated to a solid
  7. dissolutionThe solid was dissolved in water
  8. additionammonium chloride added
  9. extractionThe precipitated oil was extracted with dichloromethane
  10. dry with materialdried over anhydrous magnesium sulphate
  11. customevaporated
  12. customto leave a solid which
  13. customwas recrystallised from acetonitrile

Sources & evidence

ORD record
ord-addc622addb74b33917f9d6268941acb
Source dataset
uspto-grants-1980_04
Patent number
US04197241

Reaction notes

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