1-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde → HCID 178518166, compound

HRID 1620629Notes

Reaction equation

HRID 1620629 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH:12]=O)[CH2:8][CH2:7]1.[OH:24][C@@H:25]1[CH2:30][CH2:29][CH2:28][CH2:27][C@H:26]1[NH:31][C:32]1[CH2:36][S:35][C:34](=[O:37])[N:33]=1>CC(O)C.C([O-])(=O)C.[NH2+]1CCCCC1>[F:1][C:2]([F:22])([F:23])[C:3]1[CH:17]=[C:16]([C:18]([F:20])([F:21])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:7][CH2:8][CH:9](/[CH:12]=[C:36]2/[C:32]([NH:31][C@@H:26]3[CH2:27][CH2:28][CH2:29][CH2:30][C@H:25]3[OH:24])=[N:33][C:34](=[O:37])[S:35]/2)[CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 866786631-[2,4-Bis(trifluoromethyl)benzyl]piperidine-4-carbaldehydeHCID 178518169HCID 178518169, compound

Product 1

HCID 178518166HCID 178518166, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolvent2×HCID 3014295Piperidinium acetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (549 mg) in 2-propanol (5 mL) were added a solution of 4-[(trans-2-hydroxycyclohexyl)amino]thiazol-2(5H)-one (520 mg) in 2-propanol (5 mL) and piperidinium acetate (240 mg). The reaction mixture was stirred at 80° C. overnight, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (557 mg).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  3. customrecrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-7e73d7a908cf4b87a2b89e1dccc73bbc
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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