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Triethylamine → 1-Benzyl-4-[N-methyl-N-(3-(1-ethoxycyclopropylamino)-2-pyridinyl)amino]piperidine

HRID 361824
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인쇄 미리보기

반응식

HRID 361824 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:22])[C:15]2[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:24]1([O:27][CH2:28][CH3:29])[CH2:26][CH2:25]1.C(N(CC)CC)C>O1CCCC1.C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:22])[C:15]2[C:20]([NH:21][C:24]3([O:27][CH2:28][CH3:29])[CH2:26][CH2:25]3)=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 106616501-Benzyl-4-[N-methyl-N-(3-amino-2-pyridinyl)amino]piperidineHCID 133803211-Bromo-1-ethoxycyclopropane

생성물 1

HCID 106435211-Benzyl-4-[N-methyl-N-(3-(1-ethoxycyclopropylamino)-2-pyridinyl)amino]piperidine

시약·촉매·용매 2

HCID 6344Dichloromethane용매
HCID 8028
Tetrahydrofuran
용매

실험 절차

A mixture of 1-benzyl-4-[N-methyl-N-(3-amino-2-pyridinyl)amino]piperidine (EXAMPLE 122, 825 mg), 1-bromo-1-ethoxycyclopropane (919 mg) and triethylamine (0.78 ml) in dry tetrahydrofuran (1.4 ml) under nitrogen is refluxed for 48 hrs, cooled to 20°-25°, diluted with methylene chloride (30 ml), washed with saline (10 ml), dried over sodium sulfate and concentrated under reduced pressure to give the crude product. The residue is chromatographed (silica gel, 70-230 mesh, 140 g; eluting with a gradient of methanol/methylene chloride (1/99-5/95)) to give the title compound, NMR (CDCl3) 7.80, 7.41, 7.25, 6.93, 5.62, 3.51, 3.48, 3.03, 2.87, 2.60, 1.98, 1.71, 1.64, 1.13 and 0.85δ.

후처리

  1. temperatureis refluxed for 48 hrs
  2. temperaturecooled to 20°-25°
  3. washwashed with saline (10 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give the crude product
  7. customThe residue is chromatographed (silica gel, 70-230 mesh, 140 g
  8. washeluting with a gradient of methanol/methylene chloride (1/99-5/95))

출처 및 근거

ORD 기록
ord-24bb735a9e6a41e986e4d7d6a9af0f11
출처 데이터셋
uspto-grants-1999_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05866589

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