Sodium Carbonate → HCID 22596144, compound

HRID 2301944Notes

Reaction equation

HRID 2301944 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH2:16])[CH2:12][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: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:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:12][CH2:13][CH2:14][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 22596141HCID 22596141, compound

Product 1

HCID 22596144HCID 22596144, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 1-(3′,4′-dimethoxyphenyl)pentylamine (0.3 grams, 1.34 mmol) and sodium carbonate (0.15 grams, 1.45 mmol) in a mixture of water (10 milliliters) and acetonitrile (10 milliliters) was added N-carbethoxyphthalimide (0.29 grams, 1.34 mmol). The resulting solution was stirred for 3 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 to afford 0.41 grams of crude product as an oil. The crude product was purified by flash chromatography (silica gel, 30% ethyl acetate/hexane) to afford 0.18 grams (38%) of the product as an oil: 1H NMR (CDCl3) δ7.88-7.63(m, 4H), 7.20-7.07(m, 2H),6.82-6.76(m, 1H), 5.34-5.18(m, 1H), 3.89(s, 3H), 3.85(s, 3H),2.66-2.43(m, 1H),2.40-2.17(m, 1H), 1.50-1.20(m, 2H), 0.96-0.81(m, 3H). 13C NMR (CDCl3) δ1.68.5, 148.8, 148.5, 133.8, 132.5, 131.9, 123.1, 120.6, 111.6, 110.8, 55.9, 55.8, 55.0, 30.9, 29.2, 22.3, 13.9.

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
  6. customto afford 0.41 grams of crude product as an oil
  7. customThe crude product was purified by flash chromatography (silica gel, 30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-613fecbff44e4eb59e07857a64bbe779
Source dataset
uspto-grants-2002_08
Patent number
US06429221B1

Reaction notes

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