1-Methylpiperazine → HCID 58638516, compound

HRID 646918Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH3:14])[CH2:10][CH2:9]2)[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=1.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>>[CH3:14][CH:11]1[CH2:12][CH2:13][N:8]([C:6]2[C:5]([N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=[C:2]([N:22]3[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]3)[N:7]=2)[CH2:9][CH2:10]1

Participants

Reactant 2

HCID 531671-Methylpiperazine

HCID 431526786'-Chloro-4-methyl-3'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl

Product 1

HCID 58638516HCID 58638516, compoundYield 77.1%

Conditions

Temperature: 145 °C

Procedure

A flask was charged with 6′-chloro-4-methyl-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl (210 mg, 0.820 mmol) (as prepared in the previous step), and 1-methylpiperazine (182 μL, 1.65 mmol) and the mixture was stirred at 145° C. for 3 h. Purification of the resulting residue by silica gel preparative TLC eluting with 10% methanol in dichloromethane yielded 202 mg (77%) of the title compound as yellow glass. 1H-NMR (400 MHz, CDCl3): δ 8.19 (d, 1H, J=9.2 Hz), 6.03 (d, 1H, J=9.2 Hz), 3.82 (m, 2H), 3.70 (m, 4H), 2.98 (m, 2H), 2.48 (m, 2H), 2.34 (s, 3H), 1.71-1.60 (m, 3), 1.35 (m, 2H), 0.97 (d, 3H, J=6.3 Hz). LC-MS (ESI, m/z): Calcd. for C16H26N5O2, 320.2 (M+H); found: 320.1.

Workup

customPurification of the resulting residue by silica gel preparative TLC
washeluting with 10% methanol in dichloromethane

Sources & evidence

ORD record: ord-77a23d180cf5424da0274788850da54e
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705042B2

Reaction notes

Loading…