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

HRID 844148Notes

Reaction equation

HRID 844148 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-55125023bcf44ac08491b2234f506c63
Source dataset
uspto-grants-2002_04
Patent number
US06380221B1

Reaction notes

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