Acetyl chloride → Tert-butyl 4-[3-(acetylamino)phenyl]-1-piperidinecarboxylate

HRID 1269135노트

반응식

HRID 1269135 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[C:28](Cl)(=[O:30])[CH3:29]>C1COCC1>[C:28]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13]2)[CH:5]=[CH:6][CH:7]=1)(=[O:30])[CH3:29]

참가 물질

5

반응물 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 22049268tert-Butyl 4-(3-aminophenyl)piperidine-1-carboxylate

생성물 1

HCID 22049422Tert-butyl 4-[3-(acetylamino)phenyl]-1-piperidinecarboxylate수율 99%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Into a solution of 14.6 g (52.6 mmol) of tert-butyl 4-[3-(amino)phenyl]-1-piperidinecarboxylate and 14.7 mL (105 mmol) of triethylamine in 120 mL THF at 0° C. was slowly added 4.5 mL (63.1 mmol) of acetyl chloride. The reaction mixture was stirred at room temperature for 2 hours and concentrated in vacuo. The residue was dissolved in CH2Cl2 and washed with H2O, followed by brine. The organic layer was dried over MgSO4 and concentrated in vacuo to give 16.6 g (52.1 mmol, 99%) of desired product: 1H NMR (400 MHz, CDCl3) δ 7.41–7.20 (m, 3H), 6.94 (d, 1H, J=7.5 Hz), 4.21 (m, 2H), 2.75 (m, 2H), 2.62 (m, 1H), 2.16 (s, 3H), 1.78 (m, 2H), 1.56 (m, 2H), 1.48 (s, 9H).

후처리

  1. customat 0° C.
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2
  4. washwashed with H2O
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-41d8044313374353b9cca9cc3c3e93f1
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199135B2

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