Water → HCID 14748414, compound

HRID 1649723Notes

Reaction equation

HRID 1649723 reaction equation
[CH2:1]([C:8]1[CH:13]=[C:12](Cl)[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].O>ClCCl.C(OCC)C>[CH2:1]([C:8]1[CH:13]=[C:12]([N:19]2[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]2)[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 14748413HCID 14748413, compound

Product 1

HCID 14748414HCID 14748414, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-benzyl-4-chloropyridine (0.480 q; see Example 1) and N-methylpiperazine (1.0 ml) is heated at 125° under an inert atmosphere for 17 hours. Upon cooling to room temperature, the mixture produces a crystalline mass. The crude solid is treated with saturated aqueous potassium carbonate (5 ml), water (2 ml), diethyl ether (5 ml) and dichloromethane (5 ml). The organic layer is separated, dried and concentrated to an oil. Excess N-methylpiperazine is removed by drying the oil at 45° under high vacuum (10 torr), giving the title compound as a viscous oil. Structure assignment is confirmed by nmr spectroscopy. nmr (CDCl3): δ (ppm) 2.34 (s, 3H); 2.48 (dd, 4H); 3.28 (dd, 4H); 4.07 (s, 2H); 6.5 (m, 3H); 7.26 (m, 4H); 8.22 (d, 1H).

Workup

  1. temperatureis heated at 125° under an inert atmosphere for 17 hours
  2. customthe mixture produces a crystalline mass
  3. customThe organic layer is separated
  4. customdried
  5. concentrationconcentrated to an oil
  6. customExcess N-methylpiperazine is removed
  7. customby drying the oil at 45° under high vacuum (10 torr)

Sources & evidence

ORD record
ord-af9e73a062a34244b4e81de6159c19c9
Source dataset
uspto-grants-1990_05
Patent number
US04921857

Reaction notes

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