Trifluoroacetic acid → 1-Benzyl-4-((benzothiazol-2-yl)methyl)piperidine

HRID 1386782Notes

Reaction equation

HRID 1386782 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15](O)=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[SH:32].[OH-].[NH4+]>O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[S:32][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[N:25]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 87132-AminothiophenolHCID 14923Ammonium HydroxideHCID 10633397HCID 10633397, compound

Product 1

HCID 211807101-Benzyl-4-((benzothiazol-2-yl)methyl)piperidineYield 86.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1.2 g of (1-benzyl-piperidin-4-yl)acetic acid.TFA, (from EXAMPLE 163, Step C) and 433 mg of 2-aminothiophenol was treated with 10 mL of polyphosphoric acid. After stirring at 120° C. for 18 h, the syrup was poured onto ice and H2O, maintaining the temperature of the aqueous mixture below 10° C. The resulting dark brown solution was made basic with ammonium hydroxide. The aqueous mixture was extracted with EtOAc (3×). The combined organic extracts were washed with sat'd NaCl and dried over MgSO4. Concentration afforded 962 mg of the title compound as a oil.

Workup

  1. temperaturemaintaining the temperature of the aqueous mixture below 10° C
  2. extractionThe aqueous mixture was extracted with EtOAc (3×)
  3. washThe combined organic extracts were washed with sat'd NaCl
  4. dry with materialdried over MgSO4
  5. concentrationConcentration

Sources & evidence

ORD record
ord-ba49c910ae9f41e9a295a938f3ba2fa7
Source dataset
uspto-grants-2001_07
Patent number
US06265434B1

Reaction notes

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