Ethyl Acetate → ethyl (2S)-1-(1,3-benzothiazol-2-yl)-2-piperidinecarboxylate

HRID 412664Notes

Reaction equation

HRID 412664 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[C:17]([O:19][CH2:20][CH3:21])=[O:18].Cl.C(N(CC)CC)C.C(OCC)(=O)C>C1(C)C(C)=CC=CC=1.[Cu]>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11130Triethylamine hydrochlorideHCID 119872-ChlorobenzothiazoleHCID 736055Ethyl (2S)-2-piperidinecarboxylate

Product 1

HCID 57016205ethyl (2S)-1-(1,3-benzothiazol-2-yl)-2-piperidinecarboxylateYield 81.9%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7237O-XyleneSolvent

Procedure

2-Chloro-1,3-benzothiazole (503 mg) was added to a suspension of ethyl (2S)-2-piperidinecarboxylate (471 mg) [J.A.C.S. (1993), 115(22), 9925-9938], triethylamine hydrochloride (414 mg) and copper powder (38 mg) in xylene (5 ml). The reaction mixture was refluxed for 28 hours, after which time ethyl acetate (20 ml) was added to the cooled mixture and the solids filtered off. The organic layer was washed with water, dried over magnesium sulphate and the solvent removed under reduced pressure to afford ethyl (2S)-1-(1,3-benzothiazol-2-yl)-2-piperidinecarboxylate (705 mg) as a brown solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 28 hours
  2. filtrationthe solids filtered off
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-dc04ecab06f84771aa20652422f9cdc2
Source dataset
uspto-grants-2003_05
Patent number
US06562964B1

Reaction notes

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