Sodium Carbonate → 10-Azatricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien4-ol-hydrochloride

HRID 457443Notes

Reaction equation

HRID 457443 reaction equation
FC(F)(F)C([N:5]1[CH2:15][CH:14]2[CH2:16][CH:7]([C:8]3[CH:9]=[CH:10][C:11]([OH:17])=[CH:12][C:13]=32)[CH2:6]1)=O.C([O-])([O-])=O.[Na+].[Na+].C(OCC)(=O)C.[ClH:32]>CO.O>[ClH:32].[CH:14]12[CH2:16][CH:7]([CH2:6][NH:5][CH2:15]1)[C:8]1[CH:9]=[CH:10][C:11]([OH:17])=[CH:12][C:13]2=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 218647432,2,2-trifluoro-1-(7-hydroxy-4,5-dihydro-1H-1,5-methanobenzo[d]azepin-3(2H)-yl)ethanoneHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 2186470010-Azatricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien4-ol-hydrochloride

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
65 °C

Procedure

2,2,2-Trifluoro-1-(4-hydroxy-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-ethanone (50 mg, 0.184 mmol) was dissolved in methanol/H2O (3/1, 5 mL), treated with Na2CO3(s) (40 mg, 0.369 mmol) and warmed to 65° C. for 2 hours. The mixture was concentrated, diluted with H2O and extracted with CH2Cl2 (3×20 mL) then dried through a cotton plug. Filtration through a Silica gel plug provided an oil (10% methanol/CH2Cl2) which was treated with 3N HCl ethyl acetate (3 mL) then concentrated, dissolved in a minimum of methanol which was saturated with Et2O and stirred. After 18 hours the white crystalline product was collected by filtration (10 mg, 26%). 1H NMR (400 MHz, CDOD3)7.16 (d, J=8.0 Hz, 1H), 6.80 (d, J=2.0 Hz, 1H), 6.72 (dd, J=8.0, 2.0 Hz, 1H), 3.32–3.28 (4H), 3.09 (dd, J=14.5, 12.0 Hz, 2H), 2.32 (m, 1H), 2.03 (d, J=11.0 Hz, 1H). APCI MS m/e 176.2 [(M+1)+]. M.p. 308 (dec.)° C.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with H2O
  3. extractionextracted with CH2Cl2 (3×20 mL)
  4. customthen dried through a cotton plug
  5. filtrationFiltration through a Silica gel plug
  6. customprovided an oil (10% methanol/CH2Cl2) which
  7. concentrationthen concentrated
  8. dissolutiondissolved in a minimum of methanol which
  9. filtrationAfter 18 hours the white crystalline product was collected by filtration (10 mg, 26%)

Sources & evidence

ORD record
ord-07c6942f162c42a8928691fe9d517cf6
Source dataset
uspto-grants-2007_03
Patent number
US07186870B2

Reaction notes

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