3,4-Dichloroamphetamine

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3,4-Dichloroamphetamine
Clinical data
ATC code
  • none
Identifiers
  • 1-(3,4-dichlorophenyl)propan-2-amine
JSmol)
  • Clc1ccc(CC(N)C)cc1Cl
  • InChI=1S/C9H11Cl2N/c1-6(12)4-7-2-3-8(10)9(11)5-7/h2-3,5-6H,4,12H2,1H3 checkY
  • Key:PUFDZMUCDFIRQY-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

3,4-Dichloroamphetamine (DCA), is an

noradrenaline into adrenaline in the body.[7][8]

Synthesis

Patent:[9] Alternate proc:[10]

The reaction of 3,4-Dichlorobenzyl Chloride [102-47-6] (1) with cyanide anion gives 3,4-Dichlorophenylacetonitrile [3218-49-3] (2). Reaction with sodium methoxide and

ethylacetate gives Alpha-Acetoxy-3,4-Dichlorobenzeneacetonitrile, CID:14318103 (3). Removal of the nitrile group in the presence of sulfuric acid gives 3,4-Dichlorophenylacetone [6097-32-1] (4). Oxime formation with hydroxylamine gives N-[1-(3,4-dichlorophenyl)propan-2-ylidene]hydroxylamine, CID:74315855
(5). Reduction of the oxime completed the synthesis of 3,4-Dichloroamphetamine (6).

See also

References

  1. S2CID 17485209
    .
  2. S2CID 6439942
    .
  3. PMID 18354055
    .
  4. PMID 20637736
    .
  5. PMID 14322972
    .
  6. PMID 14332461
    .
  7. PMID 5553744
    .
  8. PMID 16279783
    .
  9. ^ Harley M Hanson, U.S. patent 3,215,598 (1965 to Merck and Co Inc).
  10. ^ Charles Jackson Barnett, U.S. patent 4,199,525 (1980 to Eli Lilly and Co).
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