1-(2-Hydroxyethyl)piperazine → HCID 14423121, compound

HRID 476568Notes

Reaction equation

HRID 476568 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.[OH:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>>[Cl:1][C:2]1[CH:3]=[C:4]2[N:10]([CH2:11][C:12]([N:23]3[CH2:24][CH2:25][N:20]([CH2:19][CH2:18][OH:17])[CH2:21][CH2:22]3)=[O:14])[C:9](=[O:16])[S:8][C:5]2=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 14098030HCID 14098030, compound

Product 1

HCID 14423121HCID 14423121, compoundYield 40%

Conditions

Temperature
130 °C

Procedure

A mixture of 6-chloro-1-methoxycarbonylmethyl-2-oxo-1,2-dihydrothiazolo[5,4-b]pyridine (10.32 g) and N-(2-hydroxyethyl)piperazine (10.4 g) was heated at 130° C. for 15 min. After cooling, the reaction mixture was poured into an ice-water. The precipitates obtained were extracted with chloroform. The chloroform layer was dried over magnesium sulfate, and evaporated to give crude material. The crude material was purified on a silica gel column chromatography using a mixture of methylene chloride 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 methanol and diethyl ether to give 6-chloro-2-oxo-1-{[4-(2-hydroxyethyl)-1-piperazinyl]carbonylmethyl}-1,2-dihydrothiazolo[5,4-b]pyridine (5.70 g).

Workup

  1. temperatureAfter cooling
  2. customThe precipitates obtained
  3. extractionwere extracted with chloroform
  4. dry with materialThe chloroform layer was dried over magnesium sulfate
  5. customevaporated
  6. customto give crude material
  7. customThe crude material was purified on a silica gel column chromatography
  8. additiona mixture of methylene chloride and methanol (10:1)
  9. additionThe desired fractions containing the objective compound
  10. customwere collected
  11. customevaporated
  12. customThe crude crystals obtained
  13. customwere recrystallized from a mixture of methanol and diethyl ether

Sources & evidence

ORD record
ord-84cac937ae724fc8944d076492b513b9
Source dataset
uspto-grants-1989_12
Patent number
US04885297

Reaction notes

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