Hydrochloric Acid → 3-(4-(3-Nitrophenyl)-3,6-dihydro-1(2H)-pyridinyl)-1-propanamine

HRID 2087139노트

반응식

HRID 2087139 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][NH:19]C(=O)OC(C)(C)C)[CH2:14][CH:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Cl>O1CCOCC1>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][NH2:19])[CH2:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 22049121Tert-butyl 3-(4-(3-nitrophenyl)-3,6-dihydro-1(2H)-pyridinyl)propylcarbamate

생성물 1

HCID 220487383-(4-(3-Nitrophenyl)-3,6-dihydro-1(2H)-pyridinyl)-1-propanamine수율 97%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

Into a stirred solution of 4.35 (12.0 mmol) of tert-butyl 3-(4-(3-nitrophenyl)-3,6-dihydro-1(2H)-pyridinyl)propylcarbamate in 100 ml of 1,4-dioxane at 0° C. was bubbled HCl gas for 10 minutes. The reaction mixture was allowed to warm to room temperature and the bubbling was continued for an additional 1 hour. The solvent was removed in vacuo, the residue was dissolved in 50 mL of water and was neutralized by the addition of KOH pellets. The aqueous solution was extracted with 3×80 mL of dichloromethane, the combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (silica, 9:1, dichloromethane:methanol+1% isopropyl amine) to afford 3.05 g (97.0% yield) of the desired product: 1H NMR (400 MHz, CDCl3) δ 8.24 (t, 1H, J=1.8 Hz), 8.09 (dd, 1H, J=1.8, 8.2 Hz), 7.69 (dd, 1H, J=1.8, 8.2 Hz), 7.48 (t, 1H, J=8.2 Hz), 6.24 (m, 1H), 3.21 (d, 2H, J=3.6 Hz), 2.84 (t, 2H, J=6.6 Hz), 2.75 (t, 2H, J=5.8 Hz), 2.64-2.54 (m, 4H), 1.76 (m, 2H); ESMS m/e: 262.2 (M+H)+; Anal. Calc. for C14H19N3O2 (0.06 CHCl3): C, 62.90; H, 7.16; N, 15.65. Found: C, 63.20; H, 7.16; N, 15.65.

후처리

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in 50 mL of water
  3. additionwas neutralized by the addition of KOH pellets
  4. extractionThe aqueous solution was extracted with 3×80 mL of dichloromethane
  5. dry with materialthe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (silica, 9:1, dichloromethane:methanol+1% isopropyl amine)

출처 및 근거

ORD 기록
ord-b7867c6f5c8844849b590a38dd54bdd7
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06727264B1

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