2-Benzyl-4-(2-chloro-4-pyridyl)thiazole → 2-Benzyl-4-[2-(1-piperidyl)-4-pyridyl]thiazole dihydrochloride

HRID 4356Notes

Reaction equation

HRID 4356 reaction equation
[CH2:1]([C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([Cl:19])[CH:14]=2)[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>N1CCCCC1>[ClH:19].[ClH:19].[CH2:1]([C:8]1[S:9][CH:10]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([N:16]3[CH2:17][CH2:18][CH2:13][CH2:14][CH2:15]3)[CH:14]=2)[N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 142310552-Benzyl-4-(2-chloro-4-pyridyl)thiazole

Product 1

HCID 201523612-Benzyl-4-[2-(1-piperidyl)-4-pyridyl]thiazole dihydrochlorideYield 73.5%

Reagents, catalysts & solvents 1

HCID 8082PiperidineSolvent

Procedure

A solution of 2-benzyl-4-(2-chloro-4-pyridyl)thiazole (1.00 g, 0.0035 mol) in piperidine (15 mL) was heated to reflux for 16 hours. The reaction mixture was concentrated, taken up in ether (50 mL), filtered through celite, and the filtrate washed with water (2×). The ether layer was dried and concentrated. The residue was taken up in ethanol (20 mL) and treated with an excess of dry hydrochloric acid. Careful dilution with ether afforded 2-benzyl-4-[2-(1-piperidyl)-4-pyridyl]thiazole dihydrochloride (525 mg, 49%). mp. 145° C.

Workup

  1. temperatureto reflux for 16 hours
  2. concentrationThe reaction mixture was concentrated
  3. filtrationfiltered through celite
  4. washthe filtrate washed with water (2×)
  5. dry with materialThe ether layer was dried
  6. concentrationconcentrated
  7. additiontreated with an excess of dry hydrochloric acid

Sources & evidence

ORD record
ord-4003f3bd15224084afa096bd852af473
Source dataset
uspto-grants-1988_02
Patent number
US04725606

Reaction notes

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