Sodium Iodide → HCID 16038370, compound

HRID 1819665Notes

Reaction equation

HRID 1819665 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[S:12](=[O:14])(=[O:13])[N:11]([CH:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:16][CH2:17]Cl)[C:10]3[CH:25]=[CH:26][CH:27]=[CH:28][C:9]2=3)=[CH:4][CH:3]=1.[I-].[Na+].[CH3:31][NH2:32]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]3[CH:28]=[CH:27][CH:26]=[CH:25][C:10]=3[N:11]([C@@H:15]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:16][CH2:17][NH:32][CH3:31])[S:12]2(=[O:14])=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 5238Sodium IodideHCID 6329MethylamineHCID 69059545HCID 69059545, compound

Product 1

HCID 16038370HCID 16038370, compound

Procedure

1-(4-Chloro-phenyl)-3-(3-chloro-1-phenyl-propyl)-1,3-dihydro-benzo[1,2,5]-thiadiazole 2,2-dioxide (0.12 g) was dissolved in methylamine (8M in ethanol, 20 mL), sodium iodide (58 mg, 0.39 mmol) was added and the mixture stirred for 96 hours. The mixture was concentrated in vacuo and purified via chromatography (silica, 5% methanol saturated with ammonia in chloroform) to give (3R)-3-[3-(4-chlorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-N-methyl-3-phenylpropan-1-amine as a colorless oil. The freebase was dissolved in methanol (5 mL) and treated with 2N aqueous hydrochloric acid (1.0 equivalent) and concentrated. The residue was dissolved in water and lyophilized to give 130 mg (72%) (3R)-3-[3-(4-chlorophenyl)-2,2-dioxido-2,1,3-benzothiadiazol-1(3H)-yl]-N-methyl-3-phenylpropan-1-amine as hydrochloride salt as a white powder. MS (ES) m/z 427.8.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified via chromatography (silica, 5% methanol saturated with ammonia in chloroform)

Sources & evidence

ORD record
ord-50701ce4ec8942e3afa1cfecaa09e2a1
Source dataset
uspto-grants-2009_10
Patent number
US07601744B2

Reaction notes

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