Iodoethane → (1-Ethylpiperidin-3-yl)methyl 4-methylbenzenesulfonate

HRID 2113467ノート

反応式

HRID 2113467 の反応式
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][O:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH2:3]1.[CH2:20](I)[CH3:21].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])O.[Na+]>C(#N)C>[CH2:20]([N:2]1[CH2:7][CH2:6][CH2:5][CH:4]([CH2:8][O:9][S:10]([C:13]2[CH:14]=[CH:15][C:16]([CH3:19])=[CH:17][CH:18]=2)(=[O:12])=[O:11])[CH2:3]1)[CH3:21]

参加物

6

反応物 4

HCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 131727084Toluene-4-sulfonic acid piperidin-3-ylmethyl ester, hydrochloride

生成物 1

HCID 57656762(1-Ethylpiperidin-3-yl)methyl 4-methylbenzenesulfonate収率 4.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
65 °C

実験手順

A mixture of 1 g (3.2. mmol) toluene-4-sulfonic acid piperidin-3-ylmethyl ester, hydrochloride, 1.02 g (7 mmol) ethyl iodide (commercially available) and 0.6 g (10 mmol) sodium carbonate in 20 mL acetonitrile was shaken at 65° C. over night. Sodium hydrogencarbonate aq. was added and the mixture was extracted with DCM. The combined organic fractions were evaporated to dryness and the residue was purified by preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile/water/NEt3. The combined product fractions were evaporated to yield 40 mg (4%) of the title compound as yellow oil. MS(m/e): 298 (MH+).

後処理

  1. extractionthe mixture was extracted with DCM
  2. customThe combined organic fractions were evaporated to dryness
  3. customthe residue was purified by preparative HPLC on reversed phase
  4. washeluting with a gradient
  5. customformed from acetonitrile/water/NEt3
  6. customThe combined product fractions were evaporated

出典と根拠

ORDレコード
ord-5a4d576890b54284b61aa14c21726f61
出典データセット
uspto-grants-2008_10
特許番号
US07432255B2

反応ノート

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