Triethylamine → 5-Acetyl-2-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine

HRID 2247939Notes

Reaction equation

HRID 2247939 reaction equation
Br.[C:2]([N:5]1[CH2:10][CH2:9][C:8](=O)[CH:7](Br)[CH2:6]1)(=[O:4])[CH3:3].C(N(CC)CC)C.[C:20]([NH2:23])(=[S:22])[CH3:21]>CC(C)=O>[C:2]([N:5]1[CH2:10][CH2:9][C:8]2[N:23]=[C:20]([CH3:21])[S:22][C:7]=2[CH2:6]1)(=[O:4])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723949ThioacetamideHCID 197611761-Acetyl-3-bromopiperidin-4-one hydrobromide

Product 1

HCID 150176595-Acetyl-2-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-Acetyl-3-bromo-4-piperidone hydrobromide (5.0 g, 16.6 mmol) in acetone (160 ml) was heated to 60° and treated with triethylamine (2.31 ml, 33.1 mmol) and thioacetamide (1.24 g, 16.6 mmol). The reaction mixture was heated to reflux for 24 hours, then cooled and filtered, to provide a yellow solid which was purified by column chromatography (eluant:89:10:1 chloroform: methanol: concentrated aqueous ammonium hydroxide). The title product was obtained as a yellow oil (995 mg, 5.1 mmol, 31% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 24 hours
  3. temperaturecooled
  4. filtrationfiltered
  5. customto provide a yellow solid which
  6. customwas purified by column chromatography (eluant:89:10:1 chloroform: methanol: concentrated aqueous ammonium hydroxide)

Sources & evidence

ORD record
ord-9fb39ba67aab4938b5bb3356eea3b679
Source dataset
uspto-grants-1991_08
Patent number
US05037834

Reaction notes

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