Tert-butyl 3-(2-(benzo[d]isothiazol-3-ylamino)ethylcarbamoyl)piperidine-1-carboxylate → N-(2-(benzo[d]isothiazol-3-ylamino)ethyl)piperidine-3-carboxamide

HRID 502545Notes

Reaction equation

HRID 502545 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][CH2:11][CH2:12][NH:13][C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]2)=[O:15])=[N:2]1>FC(F)(F)C(O)=O.ClCCl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([NH:10][CH2:11][CH2:12][NH:13][C:14]([CH:16]2[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]2)=[O:15])=[N:2]1

Participants

4

Reactant 1

HCID 11854495Tert-butyl 3-(2-(benzo[d]isothiazol-3-ylamino)ethylcarbamoyl)piperidine-1-carboxylate

Product 1

HCID 11856088N-(2-(benzo[d]isothiazol-3-ylamino)ethyl)piperidine-3-carboxamideYield 97.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 3-(2-(benzo[d]isothiazol-3-ylamino)ethylcarbamoyl)piperidine-1-carboxylate (360 mg, 0.89 mmol) in trifluoroacetic acid (2 mL) and dichloromethane (2 mL) was cooled to 0° C. and stirred for 2 h. The reaction mixture was then concentrated under reduced pressure and lyophilized to yield N-(2-(benzo[d]isothiazol-3-ylamino)ethyl)piperidine-3-carboxamide as a yellow oil (265 mg). MW=304 confirmed by LC-MS, tr=2.39 min (Method B) MH+=305.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-a1e0bb617dd24cb98249043435ab0073
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

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