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

HRID 1760565노트

반응식

HRID 1760565 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

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%.

후처리

  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)

출처 및 근거

ORD 기록
ord-7e7b00e8b84d4037b0c11ef6c3a4c569
출처 데이터셋
uspto-grants-2005_01
특허 번호
US06844359B2

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