Sodium bis(2-methoxyethoxy)aluminum hydroxide → HCID 22756093, compound

HRID 65839Notes

Reaction equation

HRID 65839 reaction equation
[OH-].COCCO[Al+]O[CH2:9][CH2:10]OC.[Na+].[OH-].COC1C=C([CH2:23][NH:24][CH2:25]CCNCCCCNCCCNCC2C=CC(O)=C(OC)C=2)C=CC=1O.CN(CC([C:55]1[C:66]2[CH:65]3[CH2:67][CH:60]([NH:61][CH2:62][C:63]4[CH:71]=[CH:70][CH:69]=[CH:68][C:64]=43)[C:59]=2[CH:58]=[CH:57][CH:56]=1)=O)C>C1C=CC=CC=1>[CH3:23][N:24]([CH3:25])[CH2:9][CH2:10][N:61]1[CH2:62][C:63]2[CH:64]=[CH:68][CH:69]=[CH:70][C:71]=2[CH:58]2[CH2:59][CH:60]1[C:67]1[CH:65]=[CH:66][CH:55]=[CH:56][C:57]=12

Participants

4

Reactant 2

HCID 86736195Sodium bis(2-methoxyethoxy)aluminum hydroxideHCID 131711360HCID 131711360, compound

Product 1

HCID 22756093HCID 22756093, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Add a 1M benzene solution of sodium bis(2-methoxyethoxy)aluminum hydroxide (Red-Al®)(5.3 ml.) dropwise with stirring at room temperature to a solution of dl-6-(dimethylaminoacetyl)-5,6,7,12-tetrahydro-5,12-methanodibenz[c,f]azocine (2.8 g. of the free base) in benzene (27 ml.) over 0.5 hours. Reflux for 2 hours, cool, stir at room temperature then quench by careful addition of saturated aqueous ammonium chloride solution (1.85 ml.) dropwise with stirring. Filter and evaporate the filtrate in vacuo. Dissolve the residue in methylene chloride, wash with water, brine then dry and evaporate the solvent in vacuo to obtain 2.79 g. of the free base of the title product as a viscous oil. Treat the free base with two equivalents of fumaric acid in acetone to obtain the title product as the difumarate salt, m.p. 169°-171.5° C.

Workup

  1. temperatureReflux for 2 hours
  2. temperaturecool
  3. customthen quench by careful addition of saturated aqueous ammonium chloride solution (1.85 ml.) dropwise
  4. stirringwith stirring
  5. filtrationFilter
  6. customevaporate the filtrate in vacuo
  7. dissolutionDissolve the residue in methylene chloride
  8. washwash with water, brine
  9. customthen dry
  10. customevaporate the solvent in vacuo
  11. customto obtain 2.79 g

Sources & evidence

ORD record
ord-5a5404b88ab74d1990e08582ad5f13a2
Source dataset
uspto-grants-1978_12
Patent number
US04129561

Reaction notes

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