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

HRID 646919ノート

反応式

HRID 646919 の反応式
[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

参加物

6

反応物 3

HCID 25517Ammonium Chloride2 回HCID 516892Sodium BicarbonateHCID 58638516HCID 58638516、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 23925Iron触媒2 回HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1c75d8005a734961bc33374ccb2481ff
出典データセット
uspto-grants-2010_04
特許番号
US07705042B2

反応ノート

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