Ammonium Chloride → 4-methyl-6'-(4-methyl-piperazin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-3'-ylamine

HRID 646919노트

반응식

HRID 646919 반응식
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:13]([N+:14]([O-])=O)=[CH:12][CH:11]=[C:10]([N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)[N:9]=2)[CH2:4][CH2:3]1.[Cl-].[NH4+].C(=O)(O)[O-].[Na+]>[Fe].CO>[CH3:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]2[C:13]([NH2:14])=[CH:12][CH:11]=[C:10]([N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)[N:9]=2)[CH2:6][CH2:7]1

참가 물질

6

반응물 3

HCID 25517Ammonium Chloride2회HCID 516892Sodium BicarbonateHCID 58638516HCID 58638516, 화합물

생성물 1

HCID 586385234-methyl-6'-(4-methyl-piperazin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-3'-ylamine수율 87%

시약·촉매·용매 2

HCID 23925Iron촉매2회HCID 887Methanol용매

실험 절차

A flask was charged with 4-methyl-6′-(4-methyl-piperazin-1-yl)-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl (101 mg, 0.320 mmol), methanol (10 mL), ammonium chloride (171 mg, 3.20 mmol), and iron powder (88 mg, 1.6 mmol) and refluxed for 10 h. Additional amounts of ammonium chloride (171 mg, 3.20 mmol) and iron powder (88 mg, 1.6 mmol) were added after 2.5 h and 6 h during the reflux operation. The cooled mixture was poured into satd aq sodium bicarbonate (100 mL), extracted with dichloromethane (4×20 mL), and the organic layers were dried over Na2SO4. The solvents were removed in vacuo to yield 80 mg (87%) of the title compound as a green glass. 1H-NMR (400 MHz, CDCl3): δ 6.89 (d, 1H, J=8.3), 6.21 (d, 1H, J=8.3 Hz), 3.45-3.36 (m, 8H), 2.71 (m, 2H), 2.54 (m, 4H), 2.34 (s, 3H), 1.74-1.71 (m, 2H), 1.52 (m, 1H), 1.31 (m, 2H), 0.98 (d, 3H, J=6.5 Hz). LC-MS (ESI, m/z): Calcd. for C16H28N5, 290.2 (M+H); found: 290.2.

후처리

  1. temperaturerefluxed for 10 h
  2. extractionextracted with dichloromethane (4×20 mL)
  3. dry with materialthe organic layers were dried over Na2SO4
  4. customThe solvents were removed in vacuo

출처 및 근거

ORD 기록
ord-1c75d8005a734961bc33374ccb2481ff
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705042B2

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