Piperidine → HCID 10342137, compound

HRID 2103096Notes

Reaction equation

HRID 2103096 reaction equation
[C:1]1([C:7]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:11][C:10]3[CH:12]=[CH:13][C:14]([S:16](Cl)(=[O:18])=[O:17])=[CH:15][C:9]=3[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[C:1]1([C:7]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:11][C:10]3[CH:12]=[CH:13][C:14]([S:16]([N:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]4)(=[O:18])=[O:17])=[CH:15][C:9]=3[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 22475110HCID 22475110, compound

Product 1

HCID 10342137HCID 10342137, compoundYield 52.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2-diphenyl-benzo[1,3]dioxole-5-sulfonyl chloride (3.36 g, 9 mmol) was dissolved in methylene chloride (135 ml). Piperidine (1.33 ml, 13.5 mmol) and ethyldiisopropyl amine (2.3 ml, 13.5 mmol) were added at room temperature. The reaction was stirred at room temperature overnight and washed twice with 1N aqueous HCl solution, twice with 1N aqueous NaOH solution and once with brine. The organic layer was dried over sodium sulfate and filtered. The solvent was evaporated and the residue was purified by column chromatography (4/1 hexane/ethyl acetate eluant). The product was suspended in diethyl ether and filtered to yield a white crystalline solid (1.98 g, 52 %). m.p.: 163-164° C.

Workup

  1. washwashed twice with 1N aqueous HCl solution, twice with 1N aqueous NaOH solution and once with brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customThe solvent was evaporated
  5. customthe residue was purified by column chromatography (4/1 hexane/ethyl acetate eluant)
  6. filtrationfiltered

Sources & evidence

ORD record
ord-69c6f597f9bf4faf9aeee52413e856ad
Source dataset
uspto-grants-2009_08
Patent number
US07576088B2

Reaction notes

Loading…