Sodium Iodide → tert-Butyl piperazine-1-carboxylate

HRID 565200노트

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HRID 565200 반응식
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]

참가 물질

6

반응물 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

생성물 1

HCID 143452tert-Butyl piperazine-1-carboxylate수율 193.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-022893ad69904bbaa3719462a07a4ca1
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06172062B2

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