Morpholine → 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

HRID 646944Notes

Reaction equation

HRID 646944 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[N:16]=[C:15]([N:17]3[CH2:22][CH2:21][CH:20]([CH3:23])[CH2:19][CH2:18]3)[C:14]([N+:24]([O-:26])=[O:25])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].CCN(CC)CC.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>C(Cl)Cl>[CH3:23][CH:20]1[CH2:19][CH2:18][N:17]([C:15]2[C:14]([N+:24]([O-:26])=[O:25])=[CH:13][CH:12]=[C:11]([N:8]3[CH2:7][CH2:6][N:5]([C:3](=[O:4])[CH2:2][N:34]4[CH2:39][CH2:38][O:37][CH2:36][CH2:35]4)[CH2:10][CH2:9]3)[N:16]=2)[CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 586385062-Chloro-1-[4-(4-methyl-3'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-6'-yl)-piperazin-1-yl]-ethanone

Product 1

HCID 586385121-[4-(4-Methyl-3'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl-6'-yl)-piperazin-1-yl]-2-morpholin-4-yl-ethanoneYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-chloro-1-[4-(4-methyl-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-6′-yl)-piperazin-1-yl]-ethanone (as prepared in the previous step, 0.18 g, 0.48 mmol) in CH2Cl2 (10 mL) was treated with Et3N (0.10 mL, 0.72 mmol) and morpholine (46 μL, 0.53 mmol). The reaction was stirred at room temperature for 18.5 h. The reaction was diluted with CH2Cl2 and washed with water. The aqueous layer was extracted further with CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated in vacuo to afford the title compound (0.16 g, 76%) as a yellow solid. 1H-NMR (CDCl3; 400 MHz): δ 8.21 (d, 1H, J=9.2 Hz), 6.03 (d, 1H, J=9.2 Hz), 3.85-3.63 (m, 12H), 3.32-3.22 (m, 2H), 3.05-2.93 (m, 2H), 2.66-2.50 (m, 2H), 1.75-1.66 (m, 2H), 1.66-1.60 (m, 2H, partially obscured by water peak), 1.44-1.38 (m, 1H), 1.37-1.16 (m, 4H), 0.98 (d, 3H, J=6.4 Hz). LC-MS (ESI, m/z): Calcd. for C21H32N6O4, 433.2 (M+H), found 432.9.

Workup

  1. washwashed with water
  2. extractionThe aqueous layer was extracted further with CH2Cl2
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56ad42b1f30e4e2f903ef585e7122c65
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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