1-Methylpiperazine → 2-Methoxycarbonyl-3-chloro-4-((4-methylpiperazin-1-yl)methyl)thiophene

HRID 370079Notes

Reaction equation

HRID 370079 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[C:8]([CH2:11]Br)[C:9]=1[Cl:10])=[O:4].[CH3:13][N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[C:8]([CH2:11][N:17]2[CH2:18][CH2:19][N:14]([CH3:13])[CH2:15][CH2:16]2)[C:9]=1[Cl:10])=[O:4]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 18376575Methyl 4-(bromomethyl)-3-chlorothiophene-2-carboxylate

Product 1

HCID 183767522-Methoxycarbonyl-3-chloro-4-((4-methylpiperazin-1-yl)methyl)thiopheneYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-methoxycarbonyl-3-chloro-4-(bromomethyl)thiophene (0.20 g, 0.74 mmol) in methylene chloride (7.5 mL) was added 1-methylpiperazine (0.095 mL, 0.86 mmol) and the mixture was stirred at ambient temperature. After 16 hours, the mixture was poured onto methylene chloride (20 mL) and washed with dilute aqueous NaHCO3, water and brine, dried over Na2SO4 and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 0.085 g (40% yield) of 2-methoxycarbonyl-3-chloro-4-((4-methylpiperazin-1-yl)methyl)thiophene as a tan solid; NMR (CDCl3) 7.4 (s, 1), 3.9 (s, 3), 3.5 (s, 2), 2.3-2.7 (br m, 8), 2.2 (s, 3) ppm.

Workup

  1. additionthe mixture was poured onto methylene chloride (20 mL)
  2. washwashed with dilute aqueous NaHCO3, water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-a25d6686716d41aaa64f061ca8c1ba9a
Source dataset
uspto-grants-2000_10
Patent number
US06140351

Reaction notes

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