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

HRID 541214

反応式

HRID 541214 の反応式
[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]

参加物

4

反応物 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 682883815-(4-(4-Cyanophenyl)piperidine-1-carbonyl)-2-methylbenzoic acid2 回

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-428f99b90a60475aae5aed1fc4c48d08
出典データセット
uspto-grants-2014_10
特許番号
US08871790B2

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