Hydrochloric Acid → HCID 19087159, compound

HRID 1464688Notes

Reaction equation

HRID 1464688 reaction equation
[CH2:1]([N:4]([CH2:15][CH2:16][CH3:17])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:7][CH2:6]1)[CH2:2][CH3:3].Cl.[Br:19]Br.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.CCOC(C)=O.CCCCCC.O>[Br:19][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[O:7][CH2:6][CH:5]([N:4]([CH2:1][CH2:2][CH3:3])[CH2:15][CH2:16][CH3:17])[CH2:14]2

Participants

8

Reactant 4

HCID 313Hydrochloric Acid4×HCID 10340Sodium CarbonateHCID 24408BromineHCID 10105405HCID 10105405, compound

Product 1

HCID 19087159HCID 19087159, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

The free base of 3-(di-n-propylamino)chromane (60 mg, 0.026 mmol) was converted to the hydrochloride with HCl-saturated EtOH. The residue after evaporation of the solvent and excess HCl was dissolved in CH2Cl2 and 4 equivalents of Br2 dissolved in CH2Cl2 were added. The reaction was complete after 2 hours and water was added. The product was found in the organic layer, which was basified with 10% Na2CO3. The organic phase was dried (Na2SO4), filtered and the solvent was evaporated, yielding an oil, which was converted to the hydrochloride with HCl-saturated EtOH. Crystals were formed from EtOAc-Hexane (30 mg) melting at 120° C. GC/MS showed M+ /M+2 at m/e=310.95(10%)/312.95(10%) and the base peak pair at m/e=282.00(100%)/284.00(97%).

Workup

  1. customThe residue after evaporation of the solvent and excess HCl
  2. dissolutionwas dissolved in CH2Cl2
  3. additionwere added
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customyielding an oil, which

Sources & evidence

ORD record
ord-6f6a2c76649144019c70153002262265
Source dataset
uspto-grants-1994_04
Patent number
US05306830

Reaction notes

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