Propane → 1-Phthalimido-1-(4-methoxyphenyl)propane

HRID 2054718Notes

Reaction equation

HRID 2054718 reaction equation
CCC.[CH3:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([NH2:15])[CH2:13][CH3:14])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:31](=[O:32])[C:30]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]2[C:28]1=[O:37])(OCC)=O>O.C(#N)C>[C:28]1(=[O:37])[N:15]([CH:12]([C:9]2[CH:10]=[CH:11][C:6]([O:5][CH3:4])=[CH:7][CH:8]=2)[CH2:13][CH3:14])[C:31](=[O:32])[C:30]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]12

Participants

7

Reactant 4

HCID 6334PropaneHCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 31432871-(4-Methoxyphenyl)propan-1-amine

Product 1

HCID 120499681-Phthalimido-1-(4-methoxyphenyl)propaneYield 38.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

1-Phthalimido-1-4′-methoxyphenyl)propane. To a stirred solution of 1-(4′-methoxyphenyl)propylamine (2.5 grams, 15.2 mmol) and sodium carbonate (1.74 grams, 16.4 mmol) in a mixture of water (50 milliliters) and acetonitrile (50 milliliters) was added N-carbethoxyphthalimide (3.34 grams, 15.2 mmol). The resulting suspension was stirred for 4.5 hours at room temperature, the acetonitrile was removed in vacuo and a solid formed. The slurry was filtered and the solid was washed with water and air dried to afford 1.73 grams (39%) of crude product as a white powder. The crude product was recrystallized from hexane/ethyl acetate and dried in vacuo (60° C., <1 mm) to afford 1.71 grams (38%) of the product as white crystals: mp 85-86° C.; 1H NMR (DMSO-d6) δ 7.92-7.79 (m, 4H), 7.46-7.28 (m, 2H), 6.97-6.83 (m, 2H), 5.19-5.06 (m, 1H), 3.72 (s, 3H), 2.56-2.13 (m, 2H), 0.87 (t, J=7.3 Hz, 3H); 13C NMR (DMSO-d6) δ 167.8, 1.5, 134.6, 131.7, 131.0, 128.6, 123.1, 113.7, 55.2, 54.9, 23.8, 11.3. Anal. Calculated for C18H17NO3. Theoretical: C, 73.20; H, 5.80; N, 4.74. Found: C, 73.24; H, 5.74, N, 4.86. HPLC 100%.

Workup

  1. customthe acetonitrile was removed in vacuo
  2. customa solid formed
  3. filtrationThe slurry was filtered
  4. washthe solid was washed with water and air
  5. customdried
  6. customto afford 1.73 grams (39%) of crude product as a white powder
  7. customThe crude product was recrystallized from hexane/ethyl acetate
  8. customdried in vacuo (60° C., <1 mm)

Sources & evidence

ORD record
ord-b004b758ad7a482d9bfcce2311745250
Source dataset
uspto-grants-2008_02
Patent number
US07329761B2

Reaction notes

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