Sodium hydride → 6-[3-(4-Methyl-piperazin-1-yl)-propoxy]-nicotinonitrile

HRID 2420977Notes

Reaction equation

HRID 2420977 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][OH:11])[CH2:4][CH2:3]1.[H-].[Na+].Cl[C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][N:16]=1>>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][O:11][C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][N:16]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 792083-(4-Methyl-1-piperazine)propan-1-olHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 1

HCID 574347666-[3-(4-Methyl-piperazin-1-yl)-propoxy]-nicotinonitrileYield 47.2%

Procedure

This compound was prepared by the method described in General Procedure 5 in Example 27 using 3-(4-methyl-piperazin-1-yl)-propan-1-ol (1.0 g, 6.32 mmol), 60% sodium hydride (379 mg, 9.48 mmol), and 6-chloronicotinonitrile (876 mg, 6.32 mmol). The reaction mixture was partitioned between satd. aq. NaHCO3 (30 mL) and CHCl3 (60 mL). The organic layer was dried (Na2SO4), filtered, and concentrated. Purification by Method 1 afforded 776 mg (47%) of a beige solid. MS (ESI): mass calcd for C14H20N4O, 260.16; m/z found, 261.3 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.47 (dd, J=2.3, 0.8, 1H), 7.77 (dd, J=8.6, 2.3, 1H), 6.80 (dd, J=8.6, 0.8, 1H), 4.41 (t, J=6.6, 2H), 2.76-2.35 (m, 10H), 2.29 (s, 3H), 2.01-1.95 (m, 2H).

Workup

  1. customThis compound was prepared by the method
  2. customThe reaction mixture was partitioned between satd
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by Method 1

Sources & evidence

ORD record
ord-ce1ebd13606642479b077584e4d6c83f
Source dataset
uspto-grants-2011_06
Patent number
US07956066B2

Reaction notes

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