Water → HCID 9974286, compound

HRID 2116589Notes

Reaction equation

HRID 2116589 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 phase was extracted with chloroform. The organic phases were combined, dried and the solvent was 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. extractionthe aqueous phase was extracted with chloroform
  4. customdried
  5. customthe solvent was evaporated
  6. customFlash chromatography (silica, 10% methanol in chloroform) of the residue gave AF286 (140 mg, 15% yield)

Sources & evidence

ORD record
ord-62ebd65534144139a486a4d67c32fbd5
Source dataset
uspto-grants-2008_10
Patent number
US07439251B2

Reaction notes

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