Piperidine → HCID 23144677, compound

HRID 1967830Notes

Reaction equation

HRID 1967830 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-f7e320ba3d684ac0a1500b9a6211cd7d
Source dataset
uspto-grants-2013_04
Patent number
US08420827B2

Reaction notes

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