Sulfamide → HCID 58188966, compound

HRID 1423238Notes

Reaction equation

HRID 1423238 reaction equation
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:28](N)([NH2:31])(=[O:30])=[O:29]>O1CCOCC1>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:12][N:13]1[S:28]([NH2:31])(=[O:30])=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 82267SulfamideHCID 16725642(S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine

Product 1

HCID 58188966HCID 58188966, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Into a 25 mL round bottomed flask were added (S)-3-benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (188 mg, 0.513 mmol), sulfamide (103 mg, 1.07 mmol) and 1,4-dioxane (3 mL). The reaction mixture was refluxed under nitrogen for 3.5 h then cooled to room temperature and adsorbed onto silica gel. Purification by silica gel flash chromatography with a 0-100% EtOAc/Hexanes gradient to afford product as tan solid (165 mg, 72%). LC/MS (Method B) 3.90 min, [M+1]+ 446.

Workup

  1. temperatureThe reaction mixture was refluxed under nitrogen for 3.5 h
  2. customPurification by silica gel flash chromatography with a 0-100% EtOAc/Hexanes gradient

Sources & evidence

ORD record
ord-96f93cfc07f44bfb9d134b4c1a44af89
Source dataset
uspto-grants-2015_01
Patent number
US08927546B2

Reaction notes

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