Piperidine-1-propylamine → N-(1-Methylethyl)-N-[2-(phenylsulfonyl)ethyl]-N'-[3-(1-piperidinyl)propyl]urea

HRID 745190

反応式

HRID 745190 の反応式
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[C:23]1([S:29]([CH2:32][CH2:33][NH:34][CH:35]([CH3:37])[CH3:36])(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[CH3:36][CH:35]([N:34]([CH2:33][CH2:32][S:29]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)(=[O:30])=[O:31])[C:1]([NH:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:2])[CH3:37]

参加物

5

反応物 3

HCID 19049Piperidine-1-propylamineHCID 682631,1'-CarbonyldiimidazoleHCID 13655034N-(2-phenylsulfonylethyl)-2-propanamine

生成物 1

HCID 20152828N-(1-Methylethyl)-N-[2-(phenylsulfonyl)ethyl]-N'-[3-(1-piperidinyl)propyl]urea収率 27.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A mixture of 5.16 g (0.0319 mole) of 1,1'-carbonyldiimidazole and 4.16 g (0.029 mole) of N-(3-aminopropyl)piperidine in 400 ml of tetrahydrofuran was stirred at room temperature for 1 hr. A solution of 6.13 g (0.027 mole) of N-[2-(phenylsulfonyl)ethyl]-2-propanamine in 50 ml of tetrahydrofuran was added, and the mixture was refluxed for 20 hr. The solvent was removed in vacuo, and the residue was dissolved in a 60/40 mixture of ether and methylene chloride, respectively. The solution was extracted with three portions of water and was dried over magnesium sulfate. The solvent was removed in vacuo to give an oil. Flash chromatography on silica gel (chloroform and methanol, gradiently eluted with methanol up to 10% methanol) gave 2.89 g (27.1%) of oil: 1H NMR (CDCl3)δ7.4-8.03 (m, 5, aromatic), 6.4 (br s, 1, NH) 3.88 (m. 1, (CH3)2 (H), 3.44 (s, 4, SO2CH2CH2, 2.33 (br q, 2 NHCH2), 2.2-2.5 (m. 6. CH2CH2CH2N, and 2, 6-piperidine H), 1.3-1.83 (m, 8, (CH2CH2CH2N, and 3, 4, 5-piperidine H), 1.1 (d, 6, (CH3)2CH).

後処理

  1. temperaturethe mixture was refluxed for 20 hr
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in a 60/40 mixture of ether and methylene chloride
  4. extractionThe solution was extracted with three portions of water
  5. dry with materialwas dried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customto give an oil
  8. washFlash chromatography on silica gel (chloroform and methanol, gradiently eluted with methanol up to 10% methanol)

出典と根拠

ORDレコード
ord-689579eeeaa14da38191d46dc9e83d3b
出典データセット
uspto-grants-1986_07
特許番号
US04597902

関連ノート

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