Triethylamine → 2-Amino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole

HRID 1649843Notes

Reaction equation

HRID 1649843 reaction equation
Cl.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([CH2:8]Cl)[N:7]=1.[C:10]1([CH:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[O:17][CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C>CN(C)C=O>[NH2:2][C:3]1[S:4][CH:5]=[C:6]([CH2:8][N:21]2[CH2:22][CH2:23][CH:18]([O:17][CH:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:19][CH2:20]2)[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 732282-Thiazolamine, 4-(chloromethyl)-, hydrochloride (1:1)HCID 30175844-Benzhydryloxypiperidine

Product 1

HCID 198549372-Amino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazoleYield 70.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred mixture of 2-amino-4-chloromethylthiazole hydrochloride (0.7 g), 4-(diphenylmethoxy)piperidine (0.78 g) and triethylamine (1.82 ml) in N,N-dimethylformamide (7.8 ml) was heated at 40° C. to 45° C. for 5 hours. After cooling to ambient temperature, the reaction mixture was filtered. The filtrate was poured into water (50 ml) and extracted with ethyl acetate (80 ml×2). The extract was washed with a saturated aqueous solution of sodium chloride (30 ml) and dried over magnesium sulfate. The solvent was distilled off and the residue was subjected to column chromatography on silica gel (30 g) 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 to give 2-amino-4-[4-(diphenylmethoxy)piperidinomethyl]thiazole (0.78 g).

Workup

  1. temperaturewas heated at 40° C. to 45° C. for 5 hours
  2. filtrationthe reaction mixture was filtered
  3. additionThe filtrate was poured into water (50 ml)
  4. extractionextracted with ethyl acetate (80 ml×2)
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride (30 ml)
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent was distilled off
  8. washeluted with a mixture of chloroform and methanol (10:1 V/V)
  9. additionThe fractions containing the object compound
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a215d011ffc14004bdad469d90986a1b
Source dataset
uspto-grants-1990_05
Patent number
US04921887

Reaction notes

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