Pyridine → 2-Propionylamino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole

HRID 1649845Notes

Reaction equation

HRID 1649845 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:10][CH2:9]2)[N:6]=1.N1C=CC=CC=1.[C:34](Cl)(=[O:37])[CH2:35][CH3:36]>CN(C)C=O.ClCCl>[C:34]([NH:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:10][CH2:9]2)[N:6]=1)(=[O:37])[CH2:35][CH3:36]

Participants

6

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 198549372-Amino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole

Product 1

HCID 145008962-Propionylamino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 2-amino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole (8.04 g) and pyridine (7.72 ml) in dry N,N-dimethylformamide (80 ml) was added slowly a solution of propionyl chloride (2.76 ml) in dichloromethane (2 ml) at a temperature below 5° C. After 30 minutes, the reaction mixture was poured into ice water (800 ml) and extracted with ethyl acetate (400 ml), and the extract was dried over magnesium sulfate. The solvent was distilled off and purified by column chromatography on silica gel to give 2-propionylamino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole (8.9 g).

Workup

  1. extractionextracted with ethyl acetate (400 ml)
  2. dry with materialthe extract was dried over magnesium sulfate
  3. distillationThe solvent was distilled off
  4. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3299022a8d0e4b37b1bb0064d3319c50
Source dataset
uspto-grants-1990_05
Patent number
US04921887

Reaction notes

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