Sodium Carbonate → HCID 12049967, compound

HRID 2054716Notes

Reaction equation

HRID 2054716 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH2:13][CH:14]([NH2:16])[CH3:15])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11]C)C.C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38])(OCC)=O>O.C(#N)C>[C:29]1(=[O:38])[N:16]([CH:14]([CH2:13][C:6]2[CH:7]=[CH:8][C:9]([O:10][CH3:11])=[C:4]([O:3][CH3:1])[CH:5]=2)[CH3:15])[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]12

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 13358288HCID 13358288, compound

Product 1

HCID 12049967HCID 12049967, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 3-(3,4-diethoxyphenyl)-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) δ 7.7 (m, 4H, Ar), 6.7 (m, 3H, Ar), 4.63 (m, 1H, CH), 3.79 (s, 3H, Ome), 3.73 (s, 3H, OMe), 3.28 (dd, 1H, J=13.8, 9.8 Hz), 3.03 (dd, J=13.8, 6.5 Hz, 1H), 1.54 (d, J=6.9 Hz, 3H); 13C NMR (dmso-d6) δ 168.4, 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. concentrationThe reaction solution was 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-33f146eb6d5246d58c71bffa16edfe5d
Source dataset
uspto-grants-2008_02
Patent number
US07329761B2

Reaction notes

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