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

HRID 646919Notes

Reaction equation

HRID 646919 reaction equation
[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

Participants

6

Reactant 3

HCID 25517Ammonium Chloride2×HCID 516892Sodium BicarbonateHCID 58638516HCID 58638516, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1c75d8005a734961bc33374ccb2481ff
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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