Water → 4-(4-Nitro-3-piperidin-1-ylphenyl)morpholine

HRID 646846

반응식

HRID 646846 반응식
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]=1.[NH:17]1[CH2:22][CH2:21]S[CH2:19][CH2:18]1.[OH2:23]>>[N+:14]([C:5]1[CH:4]=[CH:3][C:2]([N:17]2[CH2:22][CH2:21][O:23][CH2:19][CH2:18]2)=[CH:7][C:6]=1[N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)([O-:16])=[O:15]

참가 물질

4

반응물 3

HCID 962WaterHCID 67164ThiomorpholineHCID 30960791-(5-Chloro-2-nitrophenyl)piperidine

생성물 1

HCID 43734724-(4-Nitro-3-piperidin-1-ylphenyl)morpholine수율 66%

반응 조건

온도
140 °C

실험 절차

A mixture of 172 mg (0.715 mmol) 1-(5-chloro-2-nitro-phenyl)-piperidine (as prepared in Example 4, step (a)) and 360 μL (3.58 mmol) of thiomorpholine were heated with stirring under Ar at 140° C. for 40 h. After cooling to RT, the mixture was poured into water (50 mL) and extracted with EtOAc (2×20 mL). The combined extracts were washed with water (3×50 mL) and brine (50 mL) and then dried (Na2SO4). Concentration and chromatography on a 10-g silica SPE column with 60% dichloromethane-hexane afforded 145 mg (66%) of the title compound as a yellow resin: Mass spectrum (ESI, m/z): Calcd. for C15H21N3O2S, 308.1 (M+H), found 308.1.

후처리

  1. temperaturewere heated
  2. temperatureAfter cooling to RT
  3. extractionextracted with EtOAc (2×20 mL)
  4. washThe combined extracts were washed with water (3×50 mL) and brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationConcentration and chromatography on a 10-g silica SPE column with 60% dichloromethane-hexane

출처 및 근거

ORD 기록
ord-f3b5db19c1274465b5cb652ebac8fd66
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705042B2

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