1,3-Dichloroacetone → Tert-butyl 4-[4-(chloromethyl)-1,3-thiazol-2-YL]piperazine-1-carboxylate

HRID 1357662Notes

Reaction equation

HRID 1357662 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)(=[S:3])[NH2:2].[Cl:17][CH2:18][C:19]([CH2:21]Cl)=O.C(=O)(O)[O-].[Na+]>ClCCCl.C(Cl)(Cl)Cl>[Cl:17][CH2:18][C:19]1[N:2]=[C:1]([N:4]2[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]2)[S:3][CH:21]=1

Participants

6

Reactant 3

HCID 107931,3-DichloroacetoneHCID 516892Sodium BicarbonateHCID 12093220tert-Butyl 4-carbamothioylpiperazine-1-carboxylate

Product 1

HCID 18186678Tert-butyl 4-[4-(chloromethyl)-1,3-thiazol-2-YL]piperazine-1-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

A solution of tert-butyl 4-thiocarbamoylpiperazine-1-carboxylate (650 mg, 2.65 mmol) and 1,3-dichloroacetone (672 mg, 5.3 mmol) in 1,2-dichloroethane was treated with sodium bicarbonate (22 mg, 2.65 mmol). The reaction mixture was stirred at 70° C. for 18 hours and then diluted with chloroform. The dilution was washed with water and brine, dried over sodium sulfate and concentrated. Product was purified from the residue on a silica gel column, using ethyl acetate/hexanes (3/7) as eluent, to provide tert-butyl 4-(4-chloromethylthiazol-2-yl)piperazine-1-carboxylate (830 mg, 100% yield). HNMR (dmso-d6): 6.92 (1H, s), 4.57 (2H, s), 3.40 (8H, m), 1.42 (9H, s).

Workup

  1. washThe dilution was washed with water and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customProduct was purified from the residue on a silica gel column

Sources & evidence

ORD record
ord-78154536c38d4ec6b90700c5fd2bd49d
Source dataset
uspto-grants-2003_07
Patent number
US06593327B2

Reaction notes

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