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

HRID 1649844Notes

Reaction equation

HRID 1649844 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9](=[O:12])[CH2:10][CH3:11])[S:6][CH:7]=1.[C:13]1([CH:19]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:20][CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:9]([NH:8][C:5]1[S:6][CH:7]=[C:3]([CH2:2][N:24]2[CH2:25][CH2:26][CH:21]([O:20][CH:19]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:22][CH2:23]2)[N:4]=1)(=[O:12])[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 30175844-BenzhydryloxypiperidineHCID 103980162-Propionylamino-4-chloromethylthiazole

Product 1

HCID 145008962-Propionylamino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazoleYield 26.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 4-chloromethyl-2-propionylaminothiazole (0.64 g), 4-(diphenylmethoxy)piperidine (0.8 g) and sodium bicarbonate (0.3 g) in N,N-dimethylformamide (8 ml) was heated at 80° to 90° C. for 2 hours. The reaction mixture was poured into ice water. The resulting precipitate was collected, washed with water and dried in vacuo. The precipitate was subjected to column chromatography on silica gel and eluted with a mixture of chloroform and methanol (10:1 V/V). The fractions containing the object compound were combined and concentrated under reduced pressure. The residue was triturated with diisopropyl ether to give white crystals. The crystals were recrystallized from a mixture of toluene and diisopropyl ether and dried under reduced pressure to give 2-propionylamino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole (0.35 g).

Workup

  1. temperaturewas heated at 80° to 90° C. for 2 hours
  2. customThe resulting precipitate was collected
  3. washwashed with water
  4. customdried in vacuo
  5. washeluted with a mixture of chloroform and methanol (10:1 V/V)
  6. additionThe fractions containing the object compound
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with diisopropyl ether
  9. customto give white crystals
  10. customThe crystals were recrystallized from a mixture of toluene and diisopropyl ether
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-1fdb981b6a1a48e49956a79e025dd182
Source dataset
uspto-grants-1990_05
Patent number
US04921887

Reaction notes

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