Hydrochloric Acid → HCID 10051474, compound

HRID 2103100Notes

Reaction equation

HRID 2103100 reaction equation
Cl.[C:2]1([CH:8]2[CH:13]=[CH:12][NH:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)C(C)C)C.[C:23]1([C:29]2([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[O:33][C:32]3[CH:34]=[CH:35][C:36]([S:38](Cl)(=[O:40])=[O:39])=[CH:37][C:31]=3[O:30]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>C(Cl)Cl>[C:42]1([C:29]2([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[O:33][C:32]3[CH:34]=[CH:35][C:36]([S:38]([N:11]4[CH2:10][CH:9]=[C:8]([C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)[CH2:13][CH2:12]4)(=[O:39])=[O:40])=[CH:37][C:31]=3[O:30]2)[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 224750674-Phenyl-1,2,3,4-tetrahydropyridine--hydrogen chloride (1/1)HCID 22475110HCID 22475110, compound

Product 1

HCID 10051474HCID 10051474, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Phenyl-1,2,3,4-tetrahydropyridine hydrochloride (15.92 mg, 0.10 mmol) was suspended in methylene chloride (2 ml). Ethyldiisopropylamine (0.035 ml, 0.20 mmol) was added and the solution was shaken for 10 minutes at room temperature. 2,2-Diphenyl-benzo[1,3]dioxole-5-sulfonyl chloride (37.28 mg, 0.10 mmol) was added and the reaction was shaken at room temperature for 12 hours. Aqueous HCl (0.1 N, 1.0 ml) was added and the mixture shaken for 30 minutes, the aqueous layer removed and the organic phase concentrated and purified by preparative reverse phase HPLC (YMC, ODS-AQ packing; 20%→95% CH3CN/H2O) to yield the sulfonamide (23.6 mg, 48%).

Workup

  1. stirringthe reaction was shaken at room temperature for 12 hours
  2. stirringthe mixture shaken for 30 minutes
  3. customthe aqueous layer removed
  4. concentrationthe organic phase concentrated
  5. custompurified by preparative reverse phase HPLC (YMC, ODS-AQ packing; 20%→95% CH3CN/H2O)

Sources & evidence

ORD record
ord-fc5e3c99e31f44d2b9e55adf53493e48
Source dataset
uspto-grants-2009_08
Patent number
US07576088B2

Reaction notes

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