Piperidine → HCID 86599840, compound

HRID 2099014Notes

Reaction equation

HRID 2099014 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([CH:15]=O)=[C:11]([OH:14])[CH:12]=2)[CH2:7][CH2:6][CH2:5]1.C[O:18][C:19](=O)[CH2:20][C:21]1[N:22]=[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][N:24]2[CH:30]=1.N1CCCCC1>C1C=CC=CC=1.C(#N)C>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]2[N:24]([CH:30]=[C:21]([C:20]3[C:19](=[O:18])[O:14][C:11]4[C:10]([CH:15]=3)=[CH:9][C:8]3[CH2:7][CH2:6][CH2:5][N:4]([CH2:3][CH2:2][F:1])[C:13]=3[CH:12]=4)[N:22]=2)[CH:25]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 16413490HCID 16413490, compoundHCID 86599841HCID 86599841, compound

Product 1

HCID 86599840HCID 86599840, compoundYield 67.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6342AcetonitrileSolvent

Procedure

200 mg (0.896 mmol) 1-(2-Fluoro-ethyl)-7-hydroxy-1,2,3,4-tetrahydro-quinoline-6-carbaldehyde and 201 mg (1 eq.) (6-chloro-imidazo[1,2-a]pyridin-2-yl)-acetic acid methyl ester in 6 mL benzene and 3 mL acetonitrile are treated with 0.177 mL (2 eq.) piperidine and refluxed for 18 h. The reaction mixture is allowed to reach room temperature and the precipitate filtered, washed with acetonitrile and dried under high vacuum to yield 240 mg (67%) of desired product as a yellow powder.

Workup

  1. temperaturerefluxed for 18 h
  2. customto reach room temperature
  3. filtrationthe precipitate filtered
  4. washwashed with acetonitrile
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-7bf38d6564274c56ade1ccc0df8fc41b
Source dataset
uspto-grants-2009_08
Patent number
US07569337B2

Reaction notes

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