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

HRID 1760565Notes

Reaction equation

HRID 1760565 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-7e7b00e8b84d4037b0c11ef6c3a4c569
Source dataset
uspto-grants-2005_01
Patent number
US06844359B2

Reaction notes

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