1-Methylpiperazine → HCID 14423122, compound

HRID 476569Notes

Reaction equation

HRID 476569 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:10]([CH2:11][C:12]([O:14]C)=O)[C:9](=[O:16])[S:8][C:5]2=[N:6][CH:7]=1.[CH3:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>>[Cl:1][C:2]1[CH:3]=[C:4]2[N:10]([CH2:11][C:12]([N:21]3[CH2:22][CH2:23][N:18]([CH3:17])[CH2:19][CH2:20]3)=[O:14])[C:9](=[O:16])[S:8][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 531671-MethylpiperazineHCID 14098030HCID 14098030, compound

Product 1

HCID 14423122HCID 14423122, compoundYield 15.8%

Conditions

Temperature
130 °C

Procedure

A mixture of 6-chloro-1-methoxycarbonylmethyl-2-oxo-1,2-dihydrothiazolo[5,4-b]pyridine (2.0 g) and N-methyl-piperazine (1.6 g) was heated at 130° C. for 15 min. After cooling, the mixture was purified on a silica gel column chromatography using a mixture of chloroform and methanol (10:1). The desired fractions containing the objective compound were collected and evaporated. The crude crystals obtained were recrystallized from a mixture of chloroform and diethyl ether to give 6-chloro-2-oxo-1-[(4-methyl-1-piperazinyl)carbonylmethyl]-1,2-dihydrothiazolo[5,4-b]pyridine (0.4 g).

Workup

  1. temperatureAfter cooling
  2. customthe mixture was purified on a silica gel column chromatography
  3. additiona mixture of chloroform and methanol (10:1)
  4. additionThe desired fractions containing the objective compound
  5. customwere collected
  6. customevaporated
  7. customThe crude crystals obtained
  8. customwere recrystallized from a mixture of chloroform and diethyl ether

Sources & evidence

ORD record
ord-28b77e37065b41bd9172f852a57dbe5a
Source dataset
uspto-grants-1989_12
Patent number
US04885297

Reaction notes

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