Sodium Carbonate → 1-Phthalimido-1-(4-methoxyphenyl)propane

HRID 2301938ノート

反応式

HRID 2301938 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH2:12])[CH2:10][CH3:11])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34])(OCC)=O>O.C(#N)C>[C:25]1(=[O:34])[N:12]([CH:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:10][CH3:11])[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]12

参加物

6

反応物 3

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

生成物 1

HCID 120499681-Phthalimido-1-(4-methoxyphenyl)propane収率 38.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

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) δ7.92-7.79(m, 4H), 7.46-7.28(m,2 H), 6.97-6.83(m, 2 H), 5.19-5.06(m, 1 H), 3.72(s, 3H), 2.56-2.13(m, 2 H), 0.87(t, J=7.3 Hz, 3 H);13C NMR (DMSO-d6) δ167.8, 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%.

後処理

  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)

出典と根拠

ORDレコード
ord-bca56d89577540319a8faadb703d4d0b
出典データセット
uspto-grants-2002_08
特許番号
US06429221B1

反応ノート

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