Hydrochloric Acid → HCID 13083937, compound

HRID 1902844Notes

Reaction equation

HRID 1902844 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:13][CH2:14][CH2:15][N:16]3[CH:21]4[CH2:22][CH2:23][CH:17]3[CH2:18][C:19](=O)[CH2:20]4)[O:12]CCO2)=[CH:4][CH:3]=1.[O:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.O.Cl>CC(C)=O.C(OCC)C>[F:1][C:2]1[CH:3]=[CH:4][C:28]([C:29]([CH:19]2[CH2:18][CH:17]3[N:16]([CH2:15][CH2:14][CH2:13][C:8]([C:5]4[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=4)=[O:12])[CH:21]([CH2:22][CH2:23]3)[CH2:20]2)=[O:25])=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 13083942HCID 13083942, compound

Product 1

HCID 13083937HCID 13083937, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

To the resulting suspension is added dropwise with stirring, a solution of 3.33 g. (0.01 mol) 8-[3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl]-8-azabicyclo[3.2.1]octan-3-one in 50 ml. dry tetrahydrofuran over 20 minutes while the reaction temperature is maintained between -65° C. to -75° C. The cold reaction mixture is then permitted to stir for 11/2 hours, then allowed to warm to room temperature, after which it is placed in an oil bath at +60° to 65° for 4 hours. After standing for about 16 hours, 50 ml. of water and 100 ml. of diethyl ether is added and following agitation the layers are partitioned. The aqueous solution is extracted two additional times with diethyl ether and all ethereal extracts are combined, dried over anhydrous sodium sulfate and concentrated to afford a viscous oil. The oil is dissolved in 300 ml. of acetone, 20 ml. of 1.2 N hydrochloric acid is added and the solution stirred for 4 hours. The solution is concentrated in vacuo, 100 ml. of 3 N hydrochloric acid is added and the solution is extracted with 150 ml. of diethyl ether. The hydrochloric acid solution is made basic with 15% sodium hydroxide aqueous solution, then extracted three times with 100 ml. portions of diethyl ether.

Workup

  1. additionTo the resulting suspension is added dropwise
  2. customThe cold reaction mixture
  3. stirringto stir for 11/2 hours
  4. waitAfter standing for about 16 hours
  5. customare partitioned
  6. extractionThe aqueous solution is extracted two additional times with diethyl ether
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customto afford a viscous oil
  10. dissolutionThe oil is dissolved in 300 ml
  11. stirringthe solution stirred for 4 hours
  12. concentrationThe solution is concentrated in vacuo, 100 ml
  13. additionof 3 N hydrochloric acid is added
  14. extractionthe solution is extracted with 150 ml
  15. extractionextracted three times with 100 ml

Sources & evidence

ORD record
ord-0f79cfadc06645ab8f67ee51bda07e77
Source dataset
uspto-grants-1982_12
Patent number
US04366154

Reaction notes

Loading…