Cyclohexane → HCID 66977183, compound

HRID 712240Notes

Reaction equation

HRID 712240 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][C:18]([Br:21])=[CH:19][N:20]=1.C(N(CC)CC)C.C1CCCCC1>CN(C=O)C.CCOC(C)=O.CO>[Br:21][C:18]1[S:17][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)=[N:20][CH:19]=1

Participants

8

Reactant 4

HCID 8078CyclohexaneHCID 8471TriethylamineHCID 3123942,5-DibromothiazoleHCID 53393421Ethyl 4-ethyl-4-piperidinecarboxylate hydrochloride

Product 1

HCID 66977183HCID 66977183, compoundYield 77.3%

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 2,5-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, diluted with EtOAc (2 mL) and MeOH (2 mL). then evaporated to dryness under reduced pressure. The crude residue was purified over 12 g silica-gel using EtOAc: cyclohexane (10% to 60%) to obtain the desired product as viscous oil (110 mg, 77% 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 12 g silica-gel

Sources & evidence

ORD record
ord-b1f7b5e86d0947de8482ae1bff73231d
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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