Hydrochloric Acid → 2-Amino-4-methyl-5-[2-(4-phenylpiperidinyl)ethyl-thio]thiazole hydrochloride

HRID 36860Notes

Reaction equation

HRID 36860 reaction equation
[NH2:1][C:2]1[S:3][C:4](Br)=[C:5]([CH3:7])[N:6]=1.[C:9]1([CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][SH:23])[CH2:17][CH2:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[ClH:30]>CN(C)C=O.CO>[ClH:30].[NH2:1][C:2]1[S:3][C:4]([S:23][CH2:22][CH2:21][N:18]2[CH2:17][CH2:16][CH:15]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:20][CH2:19]2)=[C:5]([CH3:7])[N:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 129543735-Bromo-4-methyl-1,3-thiazol-2-amineHCID 199364122-(4-Phenyl-1-piperidinyl)ethyl mercaptan

Product 1

HCID 199364232-Amino-4-methyl-5-[2-(4-phenylpiperidinyl)ethyl-thio]thiazole hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

9.65 g of 2-amino-5-bromo-4-methylthiazole, 11.1 g of 2-(4-phenyl-1-piperidinyl)ethyl mercaptan and 20.7 g of potassium carbonate in 50 ml of dimethylformamide were stirred at 80° C. for 30 minutes. The mixture was poured into ice-water and extracted with methylene chloride, and the organic phase was washed with water, dried and concentrated. The residue was purified by chromatography (SiO2 ; CH2Cl2, CH3OH (0-20%)). The hydrochloride was prepared by dissolving the free base in methanol and adding ethereal HCl.

Workup

  1. extractionextracted with methylene chloride
  2. washthe organic phase was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography (SiO2 ; CH2Cl2, CH3OH (0-20%))

Sources & evidence

ORD record
ord-e58a2de72e7e48be8d5f536a83cc4485
Source dataset
uspto-grants-1995_05
Patent number
US05418235

Reaction notes

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