Ethanol → 1-[4-(3'-Amino-4-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-6'-yl)-piperazin-1-yl]-2-morpholin-4-yl-ethanone

HRID 646945Notes

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]([C:23](=[O:31])[CH2:24][N:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[CH2:19][CH2:18]3)[N:9]=2)[CH2:4][CH2:3]1.CCO.[NH4+].[Cl-].C([O-])(O)=O.[Na+]>[Fe].O>[NH2:14][C:13]1[C:8]([N:5]2[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH2:4]2)=[N:9][C:10]([N:17]2[CH2:18][CH2:19][N:20]([C:23](=[O:31])[CH2:24][N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH2:21][CH2:22]2)=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 1-[4-(4-methyl-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-6′-yl)-piperazin-1-yl]-2-morpholin-4-yl-ethanone (as prepared in the previous step, 0.16 g, 0.37 mmol) in 2:1 EtOH:water (3 mL) was treated with NH4Cl (0.20 g, 3.7 mmol) and iron powder (0.10 g, 1.8 mmol). The reaction was heated to 100° C. for 50 min then cooled to room temperature. The mixture was neutralized with saturated aqueous NaHCO3 and extracted with CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated in vacuo to afford the title compound (0.14 g, 100%), which was immediately used in the next reaction.

Workup

temperaturethen cooled to room temperature
extractionextracted with CH2Cl2
dry with materialThe combined organic layers were dried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d55045b55faa4303917640baa9f4ff1e
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705042B2

Reaction notes

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