Piperidine → HCID 23144677, compound

HRID 337499Notes

Reaction equation

HRID 337499 reaction equation
Cl[CH2:2][C:3]1[CH:29]=[CH:28][C:6]([C:7]([NH:9][C:10]2[S:11][C:12]([C:20]([CH:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[O:21])=[C:13]([C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)=[O:8])=[CH:5][CH:4]=1.[NH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>C1COCC1>[O:16]1[CH:17]=[CH:18][CH:19]=[C:15]1[C:13]1[N:14]=[C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:28]=[CH:29][C:3]([CH2:2][N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:4][CH:5]=2)[S:11][C:12]=1[C:20]([CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=[O:21]

Participants

4

Reactant 2

HCID 8082PiperidineHCID 23144430HCID 23144430, compound

Product 1

HCID 23144677HCID 23144677, compoundYield 140.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 478 (340 mg, 0.789 mmol) was suspended in THF (3 mL), and piperidine (0.390 mmol, 3.95 mmol) was added thereto, followed by stirring under heating and reflux for 1.5 hours. The solvent was distilled away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (chloroform:methanol=4:1), followed by reslurrying with diethyl ether to afford the entitled Compound 480 (262 mg, 69%) as a white solid.

Workup

  1. temperatureunder heating
  2. temperaturereflux for 1.5 hours
  3. distillationThe solvent was distilled away under reduced pressure
  4. customthe resulting residue was purified through silica gel column chromatography (chloroform:methanol=4:1)

Sources & evidence

ORD record
ord-c1d6332479e0492999952486acef8ab2
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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