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Hydrochloric Acid → 1-Benzyl-3-[3-(1-Naphthylsulfonylmethyl)-4-nitrophenoxy]-piperidine

HRID 1711420
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인쇄 미리보기

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HRID 1711420 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:25][S:26]([C:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1)(=[O:28])=[O:27].CC(C)([O-])C.[K+].Cl>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([O:14][C:15]2[CH:16]=[CH:17][C:18]([N+:21]([O-:23])=[O:22])=[C:19]([CH2:25][S:26]([C:29]3[C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[CH:32]=[CH:31][CH:30]=3)(=[O:27])=[O:28])[CH:20]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 117366081-((Chloromethyl)sulfonyl)naphthaleneHCID 222600571-Benzyl-3-(4-nitrophenoxy)piperidineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 588286341-Benzyl-3-[3-(1-Naphthylsulfonylmethyl)-4-nitrophenoxy]-piperidine수율 73.2%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

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온도
-40 °C

실험 절차

A mixture of 1-benzyl-3-(4-nitrophenoxy)piperidine (1.0 g, 3.14 mmoles) and 1-chloromethanesulfonylnaphthalene (0.9 g, 3.8 mmoles) in THF at −78° C. was treated dropwise with a solution of 1M potassium t-butoxide (9 mL, 9 mmoles) over a 30 minute period, warmed to −40° C., stirred at −40° C. for 5 hours, poured into cold 2N HCl and extracted with EtOAc. The extracts were combined, dried over Na2SO4 and concentrated under vacuum. The resultant residue was purified by normal phase HPLC on a silica column, using as eluent 40% EtOAc/hexane, to afford the title compound as an off-white solid (1.2 g, 2.3 mmoles).

후처리

  1. extractionextracted with EtOAc
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customThe resultant residue was purified by normal phase HPLC on a silica column

출처 및 근거

ORD 기록
ord-2f044691c3664492b2cad394d9cead6d
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07790751B2

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