Piperidine → HCID 86599844, compound

HRID 2099023Notes

Reaction equation

HRID 2099023 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[S:20][C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=1.N1CCCCC1>C(#N)C.C1C=CC=CC=1>[S:20]1[C:21]2[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=2[N:23]=[C:19]1[C:18]1[C:17](=[O:16])[O:13][C:7]2[C:8]([CH:9]=1)=[CH:11][CH:12]=[C:5]([N:4]([CH2:3][CH2:2][F:1])[CH3:14])[CH:6]=2

Participants

6

Reactant 3

HCID 8082PiperidineHCID 358756Methyl (1,3-benzothiazol-2-yl)acetateHCID 85863481HCID 85863481, compound

Product 1

HCID 86599844HCID 86599844, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6342AcetonitrileSolvent

Procedure

130 mg (ca. 0.65 mmol) crude 4-[(2-Fluoro-ethyl)-methyl-amino]-2-hydroxy-benzaldehyde and 202 mg (1.5 eq.) benzothiazol-2-yl-acetic acid methyl ester are dissolved in 3 mL acetonitrile and 6 mL benzene, treated with 0.14 mL (2 eq.) piperidine and heated to reflux for 45 minutes. After cooling to room temperature, the crude product is extracted with AcOEt/isopropanol 9:1 and saline, dried over sodium sulfate and evaporated. The crude product is dissolved in 20 mL methanol, and slowly concentrated down to 10 mL at 50° C. The orange crystals are filtered and dried under high vacuum to yield 110 mg (48%) desired product.

Workup

  1. temperatureheated
  2. temperatureto reflux for 45 minutes
  3. extractionthe crude product is extracted with AcOEt/isopropanol 9:1 and saline
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. dissolutionThe crude product is dissolved in 20 mL methanol
  7. concentrationslowly concentrated down to 10 mL at 50° C
  8. filtrationThe orange crystals are filtered
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-7735075ce7d0495dbc0e7306a9d15700
Source dataset
uspto-grants-2009_08
Patent number
US07569337B2

Reaction notes

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