Methanol → Methyl 5-(4-(4-cyanophenyl)piperidine-1-carbonyl)-2-methylbenzoate

HRID 541214

반응식

HRID 541214 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:18]=[CH:19][C:20]([CH3:26])=[C:21]([CH:25]=3)[C:22]([OH:24])=[O:23])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].S(=O)(=O)(O)O.[CH3:32]O>>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([C:17]3[CH:18]=[CH:19][C:20]([CH3:26])=[C:21]([CH:25]=3)[C:22]([O:24][CH3:32])=[O:23])=[O:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2]

참가 물질

4

반응물 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 682883815-(4-(4-Cyanophenyl)piperidine-1-carbonyl)-2-methylbenzoic acid2회

생성물 1

HCID 68289061Methyl 5-(4-(4-cyanophenyl)piperidine-1-carbonyl)-2-methylbenzoate수율 90%

실험 절차

To a stiffed mixture of 5-(4-(4-cyanophenyl)piperidine-1-carbonyl)-2-methylbenzoic acid (compound 39.3, 1.392 g, 4.00 mmol, 1.00 equiv) in methanol (50 mL) was added sulfuric acid (784 mg, 7.99 mmol, 2.00 equiv), dropwise. The resulting mixture was heated to reflux overnight in an oil bath. After cooling to ambient temperature, the organic solvent was removed under reduced pressure. The residue was diluted with 20 mL of EtOAc and was washed with 1×100 mL of saturated sodium bicarbonate(aq) followed by 1×100 mL of brine. The organic layer was dried (Na2SO4) and concentrated under reduced pressure to yield 1.303 g (90%) of the title compound as a white solid.

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux overnight in an oil bath
  3. customthe organic solvent was removed under reduced pressure
  4. additionThe residue was diluted with 20 mL of EtOAc
  5. washwas washed with 1×100 mL of saturated sodium bicarbonate(aq)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-428f99b90a60475aae5aed1fc4c48d08
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871790B2

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