Diisopropylethylamine → HCID 10097960, compound

HRID 2184097Notes

Reaction equation

HRID 2184097 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH:14]=[CH:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C(N(C(C)C)C(C)C)C.[C:24]1([C:30]2([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)[O:34][C:33]3[CH:35]=[CH:36][C:37]([S:39](Cl)(=[O:41])=[O:40])=[CH:38][C:32]=3[O:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(Cl)Cl>[C:43]1([C:30]2([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[O:34][C:33]3[CH:35]=[CH:36][C:37]([S:39]([N:12]4[CH2:11][CH:10]=[C:9]([C:6]5[CH:7]=[CH:8][C:3]([F:2])=[CH:4][CH:5]=5)[CH2:14][CH2:13]4)(=[O:40])=[O:41])=[CH:38][C:32]=3[O:31]2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 22475110HCID 22475110, compoundHCID 22475243HCID 22475243, compound

Product 1

HCID 10097960HCID 10097960, compoundYield 75.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4-Fluorophenyl)-1,2,3,4-tetrahydropyridine hydrochloride (2.56 g, 12 mmol) was suspended in methylene chloride (150 ml). Ethyldiisopropylamine (4.2 ml, 25 mmol) was added and the solution was stirred for 10 minutes at room temperature. 2,2-Diphenyl-benzo[1,3]dioxole-5-sulfonyl chloride (3.72 g, 10 mmol) was added and the reaction was stirred at room temperature for 2 hours. The solvent was evaporated and the residue was purified by column chromatography on silical gel (100 g, dichloromethane eluant). The product was stirred with n-hexane, filtered and dried to yield the sulfonamide as white crystals (3.86 g, 75%).

Workup

  1. stirringthe reaction was stirred at room temperature for 2 hours
  2. customThe solvent was evaporated
  3. customthe residue was purified by column chromatography on silical gel (100 g, dichloromethane eluant)
  4. stirringThe product was stirred with n-hexane
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-0b0ccb630157410293e1bbe3596cac16
Source dataset
uspto-grants-2005_05
Patent number
US06900227B2

Reaction notes

Loading…