Triethylamine → HCID 22115674, 화합물

HRID 399446

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HRID 399446 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15](OS(C(F)(F)F)(=O)=O)[CH:16]=3)[CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C([N:28]([CH2:31][CH3:32])[CH2:29]C)C.[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40]CCN)=[CH:36][CH:35]=1.[C]=[O:45]>C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:33][C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH2:32][CH2:31][NH:28][C:29]([C:15]2[CH:16]=[C:17]3[C:12]([CH:11]=[CH:10][CH:9]=[C:8]3[CH:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[CH:13][CH:14]=2)=[O:45])=[CH:36][CH:35]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 64857723-(4-Chlorophenyl)propan-1-amineHCID 22115637HCID 22115637, 화합물HCID 178418416HCID 178418416, 화합물

생성물 1

HCID 22115674HCID 22115674, 화합물수율 23%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 8857Ethyl Acetate용매

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온도
105 °C

실험 절차

A mixture of 1-(1-methylpiperidin-4-yl)-7-trifluoromethanesulfonyloxynaphthalene (0.25 g, 0.67 mmol), triethylamine (0.373 mL, 2.68 mmol), 3-(4-chlorophenyl)propylamine (0.341 mL, 2.01 mmol), and bis(triphenylphosphine)palladium chloride (0.025 g, 0.033 mmol) was blanketed with an atmosphere of carbon monoxide (balloon) and heated to 105° C. for 16 hours (h) . The reaction was diluted with ethyl acetate and filtered through celite. The filtrate was washed with water and brine, dried and concentrated. The residue was flash chromatographed on silica gel (1×3 inches packed with 75% ethyl acetate/hexane). Elution proceeded as follows: 75% ethyl acetate/hexane, 150 mL, nil; ethyl acetate, 150 mL, nil; 2% methanol/1% triethylamine/ethyl acetate, 200 mL and 2% methanol/1% triethylamine/ethyl acetate, 150 mL, 0.196 g of a yellow-oil which slowly crystallized. This material was recrystallized from chloroform/ether to give 0.064 g (23%) of 1-(1-methylpiperidin-4-yl)-7-naphthalene carboxylic acid 3-(4-chlorophenyl)propyl amide as white crystals which had mp 132°-133.5° C.; 1H NMR (250 MHz, CDCl3) δ 8.66 (s, 1H), 7.87 (d, J=8.5 Hz, 1H), 7.72 (d, J=7.5 Hz, 1H), 7.58-7.46 (m, 3H), 7.27-7.23 (m, 2H partially obscurred by the NMR solvent), 7.15 (long range coupled d, J=8.5 Hz, 2H), 6.23 (br t, 1H), 3.55 (q, J=6.5 Hz, 2H), 3.39 (sym m, 1H), 3.02 (br d, J=12 Hz, 2H), 2.72 (t, J=7.5 Hz, 2H), 2.36 (s, 3H), 2.23 (sym m, 2H), 2.04-1.89 (m, 6H). Analysis calculated for C26H29ClN2O·0.25 H2O: C, 73.40; H, 6.99; N, 6.58. Found: C, 73.30; H, 7.12; N, 6.56.

후처리

  1. filtrationfiltered through celite
  2. washThe filtrate was washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. customchromatographed on silica gel (1×3 inches packed with 75% ethyl acetate/hexane)
  6. washElution
  7. custom2% methanol/1% triethylamine/ethyl acetate, 200 mL and 2% methanol/1% triethylamine/ethyl acetate, 150 mL, 0.196 g of a yellow-oil which slowly crystallized
  8. customThis material was recrystallized from chloroform/ether

출처 및 근거

ORD 기록
ord-9b994f16e7094656b25ad31734011ce4
출처 데이터셋
uspto-grants-1998_10
특허 번호
US05821245

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