2-Bromo-1-(3-nitrophenyl)ethan-1-one → Ethyl 1-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylate

HRID 1028146Notes

Reaction equation

HRID 1028146 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)=O.[C:14]([N:17]1[CH2:22][CH2:21][CH:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]1)(=[S:16])[NH2:15]>C(O)C>[N+:11]([C:7]1[CH:6]=[C:5]([C:3]2[N:15]=[C:14]([N:17]3[CH2:22][CH2:21][CH:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]3)[S:16][CH:2]=2)[CH:10]=[CH:9][CH:8]=1)([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 752132-Bromo-1-(3-nitrophenyl)ethan-1-oneHCID 23076419Ethyl 1-carbamothioylpiperidine-4-carboxylate

Product 1

HCID 71075037Ethyl 1-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylateYield 54.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-1-(3-nitrophenyl)ethanone (621 mg, 2.54 mmol) and ethyl 1-carbamothioylpiperidine-4-carboxylate (500 mg, 2.31 mmol) in ethanol (7.7 mL) was heated to reflux for 16 hours, and then cooled to room temperature. The mixture was concentrated under reduced pressure and the resulting residue purified directly by CombiFlash (0-70% ethyl acetate/hexanes) to provide 457 mg (1.26 mmol, 49% yield) of ethyl 1-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylate as a yellow solid.

Workup

  1. temperatureto reflux for 16 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe resulting residue purified directly by CombiFlash (0-70% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a514779c524146dab3ad63b0f32f9037
Source dataset
uspto-grants-2014_05
Patent number
US08735417B2

Reaction notes

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