Piperidine → HCID 23144677, compound

HRID 1361852Notes

Reaction equation

HRID 1361852 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-e3da5ee63aa94021a230a288e9b31071
Source dataset
uspto-grants-2011_02
Patent number
US07880013B2

Reaction notes

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