Sodium Iodide → tert-Butyl piperazine-1-carboxylate

HRID 565200ノート

反応式

HRID 565200 の反応式
N1CCC(CNC(C2C3OCCOC=3C=CC=2)=O)CC1.[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][N:31](S(CCCCl)(=O)=O)[CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:23])[CH3:22].[I-].[Na+].C(N(CC)CC)C>CN(C)C=O>[C:21]([O:25][C:26]([N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 154859342,3-Dihydrobenzo[1,4]dioxine-5-carboxylic acid(piperidin-4-ylmethyl)amideHCID 227098904-tert-Butoxycarbonyl-1-[(3-chloro-1-propyl)sulfonyl]piperazine

生成物 1

HCID 143452tert-Butyl piperazine-1-carboxylate収率 193.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 2,3-dihydrobenzo[1,4]dioxine-5-carboxylic acid(piperidin-4-ylmethyl)amide (28.6 g, 104 mmol), 4-(3-chloropropane-1-sulfonyl)piperazine-1-carboxylic acid tert-butyl ester (33.9 g, 104 mmol), sodium iodide (7.8 g, 52 mmol), and triethylamine (29 mL, 209 mmol) in N,N-dimethylformamide (70 mL) was stirred at 90° C. for 4 hours. The cooled reaction mixture was partitioned between ethyl acetate and water. The ethyl acetate layer was washed with water (three times) and brine, dried (Na2SO4) and the solvents evaporated in vacuo. The crude product was purified by silica gel chromatography (5% methanol-dichloromethane) and crystallization from ethyl acetate-hexane to give 4-[3-(4-{[2,3-dihydrobenzo[1,4]dioxin-5-carbonyl)amino]-methyl}piperidin-1-yl)propane-1-sulfonyl]piperazine-1-carboxylic acid tert-butyl ester (37.5 g, 64%); m.p. 130-132° C. Analysis for C27H43N4O7 S: Calcd.: C, 57.12; H, 7.63; N, 9.87. Found: C, 57.01; H, 7.40; N, 9.94.

後処理

  1. customThe cooled reaction mixture
  2. customwas partitioned between ethyl acetate and water
  3. washThe ethyl acetate layer was washed with water (three times) and brine
  4. dry with materialdried (Na2SO4)
  5. customthe solvents evaporated in vacuo
  6. customThe crude product was purified by silica gel chromatography (5% methanol-dichloromethane) and crystallization from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-022893ad69904bbaa3719462a07a4ca1
出典データセット
uspto-grants-2001_01
特許番号
US06172062B2

反応ノート

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