Water → HCID 53880972, compound

HRID 256574Notes

Reaction equation

HRID 256574 reaction equation
[CH3:1][N:2]1[C@H:11]2[CH2:12][C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=3[C@:5]3([C@@H:10]2[CH2:9][CH2:8][CH2:7][CH2:6]3)[CH2:4][CH2:3]1.[CH:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:35]=[C:34](Cl)[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[C:23]1([C:26]2[N:35]=[C:34]([O:19][C:16]3[CH:17]=[CH:18][C:13]4[CH2:12][C@H:11]5[N:2]([CH3:1])[CH2:3][CH2:4][C@@:5]6([C:14]=4[CH:15]=3)[C@H:10]5[CH2:9][CH2:8][CH2:7][CH2:6]6)[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=2)[CH:22]=[CH:21][CH:20]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 809774-Chloro-2-phenylquinazolineHCID 5360697Dextrorphan

Product 1

HCID 53880972HCID 53880972, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The O-demethylation procedure described in Steroids 11:151 [1968] was modified for this synthesis. First, 16.1 g (62.3 mmol) of dextrorphan, 2, were dissolved in 500 mL hot acetone, to which 15.5 g (64.4 mmol) AM-ex-OL (Aldrich) and 17.13 g (123.9 mmol) potassium carbonate were added. The reaction mixture was stirred at reflux overnight under an atmosphere of argon. After cooling, the reaction mixture was poured into a separatory funnel to which 500 mL water were added. Extraction with 1×500 and 2×250 mL benzene was followed by washing the combined organics with 1×250 mL water and removing the solvent in vacuo to give 27.51 g (96%) product as a white glass which was homogeneous by TLC. Recrystallization in ethyl acetate gave pure 3 as white crystals, mp 138°-139° C. EIMS m/z 461. Anal. (C31H31N3) C, H, N.

Workup

  1. customwas modified for this synthesis
  2. additionwere added
  3. temperatureat reflux overnight under an atmosphere of argon
  4. temperatureAfter cooling
  5. additionwere added
  6. extractionExtraction with 1×500 and 2×250 mL benzene
  7. washby washing the combined organics with 1×250 mL water
  8. customremoving the solvent in vacuo

Sources & evidence

ORD record
ord-2ccbe9c2e3c04c038b5d5d96e91fd64c
Source dataset
uspto-grants-1993_11
Patent number
US05258386

Reaction notes

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