Triethylamine → Ethyl 1-(4-bromothiazol-2-yl)-4-ethyl-piperidine-4-carboxylate

HRID 712239Notes

Reaction equation

HRID 712239 reaction equation
Cl.[CH2:2]([C:4]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)[CH3:3].Br[C:16]1[S:17][CH:18]=[C:19]([Br:21])[N:20]=1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O.CO>[Br:21][C:19]1[N:20]=[C:16]([N:7]2[CH2:6][CH2:5][C:4]([CH2:2][CH3:3])([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:9][CH2:8]2)[S:17][CH:18]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27632972,4-Dibromo-1,3-thiazoleHCID 53393421Ethyl 4-ethyl-4-piperidinecarboxylate hydrochloride

Product 1

HCID 66977057Ethyl 1-(4-bromothiazol-2-yl)-4-ethyl-piperidine-4-carboxylateYield 89%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 4-ethylpiperidine-4-carboxylate hydrochloride (140 mg, 0.62 mmol) and 2,4-dibromothiazole (100 mg, 0.41 mmol) in DMF (0.3 mL) was added triethylamine (0.26 mL, 1.9 mmol) at rt and the mixture heated to 100° C. and stirred for 2 h. The mixture was cooled to rt then diluted with EtOAc (2 mL) and MeOH (2 mL) then evaporated to dryness under reduced pressure. The crude residue was purified over silica-gel using EtOAc: cyclohexane (10% to 60%) to obtain the desired product as viscous oil that solidified upon standing (127 mg, 89% yield). MS: 347.03, 349.01 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. customthen evaporated to dryness under reduced pressure
  3. customThe crude residue was purified over silica-gel

Sources & evidence

ORD record
ord-533843aa9381471fad4da40dc8f2b923
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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