Trifluoroacetic acid → 4-(Benzthiazole-2-carbonyl)piperidine

HRID 1598777Notes

Reaction equation

HRID 1598777 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]1)=[O:11].FC(F)(F)C(O)=O>C(OCC)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15337458HCID 15337458, compound

Product 1

HCID 152370094-(Benzthiazole-2-carbonyl)piperidine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Mix 4-[(2-benzothiazolyl)carbonyl]-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester (10.5 g, 30.31 mmol) and trifluoroacetic acid (75 mL) and stir at room temperature for 2 hours. Cool in an ice/water bath and add ethyl ether until a solid begins to precipitate. Stir at 0° C. for 30 minutes, collect the solid by filtration and wash with ethyl ether and recrystallize (methanol/ethyl ether) to give the title compound as a white powder; mp 195°-197° C.

Workup

  1. temperatureCool in an ice/water bath
  2. customto precipitate
  3. stirringStir at 0° C. for 30 minutes
  4. customcollect the solid
  5. filtrationby filtration
  6. washwash with ethyl ether
  7. customrecrystallize (methanol/ethyl ether)

Sources & evidence

ORD record
ord-4e25f21a227a498d91838fd3e7c6290f
Source dataset
uspto-grants-1998_04
Patent number
US05739150

Reaction notes

Loading…