(+-)-3,4-Dimethoxyamphetamine → HCID 12049967, compound

HRID 2301932Notes

Reaction equation

HRID 2301932 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH:12]([NH2:14])[CH3:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:30](=[O:31])[C:29]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]2[C:27]1=[O:36])(OCC)=O>O.C(#N)C>[C:27]1(=[O:36])[N:14]([CH:12]([CH2:11][C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH3:13])[C:30](=[O:31])[C:29]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]12

Participants

6

Reactant 3

HCID 8423(+-)-3,4-DimethoxyamphetamineHCID 10340Sodium CarbonateHCID 31187N-Carbethoxyphthalimide

Product 1

HCID 12049967HCID 12049967, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 3-(3,4-dimethoxyphenyl)-2-aminopropane (1.95 grams, 10.0 mmol) and sodium carbonate (1.06 grams, 10.0 mmol) in 50 milliliters of water was added N-carbethoxyphthalimide (2.19 grams, 10.0 mmol). After 10 minutes the reaction mixture was diluted with 40 milliliters of acetonitrile and the mixture stirred for 40 minutes The reaction solution was partially concentrated in vacuo to remove the acetonitrile. The resulting mixture of an oil and aqueous layer was extracted with methylene chloride (25 milliliters). The organic extract was dried over sodium sulfate and concentrated in vacuo to afford a crude product which was purified by flash chromatography to afford 1.73 grams (53%) of product as a thick oil which slowly solidified to a white wax: 1H NMR (dmso-d6, 250 MHz) δ7.7 (m, 4 H, Ar), 6.7 (m, 3 H, Ar), 4.63 (m, 1 H, CH), 3.79 (s, 3 H, OMe), 3.73 (s, 3 H, OMe), 3.28 (dd, 1 H, J =13.8, 9.8 Hz), 3.03 (dd, J=13.8, 6.5 Hz, 1 H), 1.54 (d, J=6.9 Hz, 3 H); 13C NMR (dmso-d6) δ168.4, 148.6, 147.4, 133.7, 131.8, 130.9, 122.9, 120.9, 111.1, 55.7, 55.6, 48.6, 39.3, 18.3. Anal. Calcd for C19H19NO2. Theoretical C, 70.14; H, 5.89; N, 4.30. Found C, 70.08; H, 5.83; N, 4.30.

Workup

  1. concentrationwas partially concentrated in vacuo
  2. customto remove the acetonitrile
  3. additionThe resulting mixture of an oil and aqueous layer
  4. extractionwas extracted with methylene chloride (25 milliliters)
  5. extractionThe organic extract
  6. dry with materialwas dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto afford a crude product which
  9. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-803f4a115cea4784bd4a06e0f547ac16
Source dataset
uspto-grants-2002_08
Patent number
US06429221B1

Reaction notes

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