Acetic Anhydride → 1-[4-(4-Aminophenyl)piperidin-1-yl]ethanone

HRID 1043316노트

반응식

HRID 1043316 반응식
C([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH3:23]CN(CC)CC.C(OC(=O)C)(=O)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([CH:11]2[CH2:12][CH2:13][N:8]([C:6](=[O:5])[CH3:23])[CH2:9][CH2:10]2)=[CH:15][CH:16]=1

참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 22049016tert-butyl 5,6-dihydro-4-(4-nitrophenyl)pyridine-1(2H)-carboxylate

생성물 1

HCID 591285511-[4-(4-Aminophenyl)piperidin-1-yl]ethanone수율 65%

시약·촉매·용매 1

HCID 21863450Trifluoroacetic acid methylene chloride용매

실험 절차

A solution of 4-(4-nitro-phenyl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (as prepared in the previous step, 304 mg, 1.00 mmol) in a 1:1 mixture of DCM/TFA (10 mL) was stirred at room temperature for 3 h and concentrated. The residue was dried in vacuo overnight, was taken up in CH2Cl2 (10 mL) and was cooled to 0° C. To this solution, Et3N (280 μL, 2 mmol) was added drop wise, followed by acetic anhydride (102 μL, 1 mmol). The resulting mixture was stirred at 0° C. for 1 h and allowed to warm to room temperature. The reaction mixture was washed with brine, and the organic layer was separated, dried and concentrated. The resulting product was reduced to obtain the title compound (143 mg, 65%) using a procedure similar to Example 4, step (d). 1H-NMR (CDCl3; 400 MHz): δ 6.97 (d, 2H, J=8.4 Hz), 6.64 (d, 2H, J=8.4 Hz), 4.75 (m, 1H), 3.93 (m, 1H), 3.13 (m, 3H), 2.66 (m, 2H), 2.12 (s, 3H), 1.84 (m, 2H), 1.57 (m, 2H).

후처리

  1. concentrationconcentrated
  2. customThe residue was dried in vacuo overnight
  3. temperaturewas cooled to 0° C
  4. stirringThe resulting mixture was stirred at 0° C. for 1 h
  5. temperatureto warm to room temperature
  6. washThe reaction mixture was washed with brine
  7. customthe organic layer was separated
  8. customdried
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-afb27bb1f1e042869e1e357b6b8d9daa
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557847B2

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