Water → HCID 9974286, compound

HRID 1825851Notes

Reaction equation

HRID 1825851 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.Cl.[CH3:10][O:11][C:12]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:13]=1[CH2:14][NH2:15].[SH:22][CH2:23][C:24](O)=[O:25].O>C1C=CC=CC=1>[CH3:10][O:11][C:12]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:13]=1[CH2:14][N:15]1[C:5]2([CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[S:22][CH2:23][C:24]1=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 1133Thioglycolic AcidHCID 740491-Methyl-4-piperidoneHCID 30843432,4-Dimethoxybenzylamine hydrochloride

Product 1

HCID 9974286HCID 9974286, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In a three-necked flask equipped with a magnetic stirrer and Dean-Stark a solution of 1-methyl-4-piperidone (0.27 ml, 2.4 mmol), 2,4-dimethoxybenzylamine hydrochloride (0.72 gr, 3.5 mmol) and mercaptoacetic acid (0.24 ml, 3.5 mmol) in benzene (5 ml) was refluxed for 3 h. The reaction mixture was cooled to room temperature, water (10 ml) was added and the organic phase was separated. The pH of the aqueous phase was adjusted to pH 10 with 2.5N aqueous sodium hydroxide solution and then the aqueous cooled to room temperature, water (10 ml) was added and the organic phase was separated. The pH of the evaporated. Flash chromatography (silica, 10% methanol in chloroform) of the residue gave AF286 (140 mg, 15% yield). 1H-NMR (CDCl3) δ 1.66 (m, 2H), 2.21 (m, 4H), 2.27 (s, 3H, NCH3), 2.77 (m, 2H), 3.64 (s, 2H, SCH2), 3.78 (s, 3H, OCH3), 3.80 (s, 3H, OCH3), 4.52 (s, 2H, NCH2),

Workup

  1. customIn a three-necked flask equipped with a magnetic stirrer
  2. customthe organic phase was separated
  3. temperaturethe aqueous cooled to room temperature
  4. additionwater (10 ml) was added
  5. customthe organic phase was separated
  6. customFlash chromatography (silica, 10% methanol in chloroform) of the residue gave AF286 (140 mg, 15% yield)

Sources & evidence

ORD record
ord-88d37b07525d4da18cf395fd3a842cf2
Source dataset
uspto-grants-2006_05
Patent number
US07049321B2

Reaction notes

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