Sodium Carbonate → HCID 22596157, compound

HRID 2301947Notes

Reaction equation

HRID 2301947 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH2:19])[CH:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:35](=[O:36])[C:34]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:33]2[C:32]1=[O:41])(OCC)=O>O.C(#N)C>[C:32]1(=[O:41])[N:19]([CH:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[C:35](=[O:36])[C:34]2=[CH:37][CH:38]=[CH:39][CH:40]=[C:33]12

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 18462748HCID 18462748, compound

Product 1

HCID 22596157HCID 22596157, compoundYield 39.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 1-(3′,4′-dimethoxyphenyl)-2-propylpentylamine (0.40 grams, 1.60 mmol) and sodium carbonate (0.18 grams, 1.72 mmol) in a mixture of water (5 milliliters) and acetonitrile (10 milliliters) was added N-carbethoxyphthalimide (0.35 grams, 1.60 mmol). The resulting solution was stirred for 2.5 hours at room temperature, the acetonitrile was evaporated and a two phase mixture resulted. The organic phase was extracted into methylene chloride, dried over magnesium sulfate and concentrated in vacuo to afford 0.6 grams of crude product as an oil. The crude product was purified by flash chromatography (silica gel, 25% ethyl acetate/hexane) to afford 0.25 grams of the product as an oil which after a few days solidified. The white solid was dried in vacuo (60° C., <1 mm) to afford 0.24 grams of pure product as a white solid: mp 100-101° C.; 1H NMR (CDCl3) δ7.84-7.59(m, 4H), 7.27-7.02(m, 2H), 6.81-6.68(m, 1H), 5.01(d, J=12 Hz, 1H), 3.89(s, 3H), 3.84(s, 3H), 3.17-2.98(m, 1H), 1.49-0.66(m, 14H). 13C NMR (CDCl3) δ168.5, 148.7, 148.4, 133.8, 131.9, 131.8, 123.1, 121.6, 112.0, 110.7, 58.9, 55.9, 55.7, 36.2, 31.9, 31.8, 18.7, 18.1, 14.6, 14.3.

Workup

  1. customthe acetonitrile was evaporated
  2. customa two phase mixture resulted
  3. extractionThe organic phase was extracted into methylene chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customto afford 0.6 grams of crude product as an oil
  7. customThe crude product was purified by flash chromatography (silica gel, 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3b5346f8d66d4089babeb59593b09e9a
Source dataset
uspto-grants-2002_08
Patent number
US06429221B1

Reaction notes

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