http://rdf.ncbi.nlm.nih.gov/pubchem/patent/FR-2174771-A1

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filingDate 1972-03-10-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1973-10-19-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber FR-2174771-A1
titleOfInvention 9-hydroxy 10,9-iminomethano anthracenes - sedatives or stimulants
abstract Compounds of formula (I) and their acid addn. salts are new: (whwere R=H, alkyl or a group -(CH2)n.NHalkyl, n= 2-5; R1 and R2= H, Cl, Br, alkyl, alkoxy, CF3 or dialkylamino R3 = O or H2; all the alkyl and alkoxy grps. contain 1-6C). The compounds are either sedatives or stimulants, and are therefor useful in psychiatry as psychoregulators. EXAMPLE 5.4 g. (II, R=CH3, R1=R2=H) were suspended in 54cc. N.NaOH and heated under reflux for 20 mins. The mixt. was cooled and 100 cc. water added. The product was extracted into CH2Cl2, washed, dried, and evapd. The residue was triturated with ether and filtered to give 4.9 g. (I, R3= O, R=CH3, R1=R2=H), m.pt. 218 degrees C. 6.7 g. of this product in 120 cc. THF were added to 75cc. of soln. of diborane in THF contg. 14.58 g./litre of diborane. The mixt. was stirred for 18 hrs. at ambient temp. then heated at 40 degrees C for 4 hrs. After cooling 70 cc. 2N NaOH were added and the mixt. refluxed for 4 hrs. The product was extracted into ethyl acetate, chromatographed on silica gel, eluting with chloroform-acetone-triethylamine (70-20-10) to give (I, R3=H2, R=CH3, R1=R2=H) m.p. 226 degrees C.
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priorityDate 1972-03-10-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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