Piperidine → HCID 86599846, compound

HRID 2099025Notes

Reaction equation

HRID 2099025 reaction equation
[F:1][CH2:2][CH2:3][N:4]([CH3:14])[C:5]1[CH:12]=[CH:11][C:8]([CH:9]=O)=[C:7]([OH:13])[CH:6]=1.C[O:16][C:17](=O)[CH2:18][C:19]1[O:20][C:21]([C:24]2[S:25][CH:26]=[CH:27][CH:28]=2)=[N:22][N:23]=1.N1CCCCC1>C1C=CC=CC=1.C(#N)C>[F:1][CH2:2][CH2:3][N:4]([CH3:14])[C:5]1[CH:6]=[C:7]2[C:8]([CH:9]=[C:18]([C:19]3[O:20][C:21]([C:24]4[S:25][CH:26]=[CH:27][CH:28]=4)=[N:22][N:23]=3)[C:17](=[O:16])[O:13]2)=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 56686505HCID 56686505, compoundHCID 85863481HCID 85863481, compound

Product 1

HCID 86599846HCID 86599846, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6342AcetonitrileSolvent

Procedure

40 mg (ca. 0.2 mmol) crude 4-[(2-Fluoro-ethyl)-methyl-amino]-2-hydroxy-benzaldehyde and 30 mg (0.13 mmol) (5-thiophen-2-yl-[1,3,4]oxadiazol-2-yl)-acetic acid methyl ester are dissolved under argon in 4 mL benzene and 2 mL acetonitrile, treated with 0.03 mL (2 eq.) piperidine and heated to reflux for 1 h. The reaction mixture is allowed to reach room temperature, evaporated, and the residue column chromatographed (silica gel, AcOEt/petroleum ether 1:1). The fluorescent, yellow product is triturated in diisopropylether, then dried under high vacuum to yield 9 mg (19%) desired product as a yellow powder.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. customto reach room temperature
  4. customevaporated
  5. customthe residue column chromatographed (silica gel, AcOEt/petroleum ether 1:1)
  6. customThe fluorescent, yellow product is triturated in diisopropylether
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-6a08fbcd16dd4b7abee502edf9491d5c
Source dataset
uspto-grants-2009_08
Patent number
US07569337B2

Reaction notes

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