Dimethyl Sulfoxide → HCID 72264651, compound

HRID 644131Notes

Reaction equation

HRID 644131 reaction equation
CS(C)=O.[OH:5][CH2:6][CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=2)[CH2:11][CH2:10]1.[NH2:27][OH:28]>O>[OH:28][N:27]=[C:23]([NH2:24])[C:22]1[CH:21]=[CH:20][C:19]([O:18][CH2:17][CH2:16][CH2:15][CH:12]2[CH2:11][CH2:10][N:9]([CH2:8][CH2:7][CH2:6][OH:5])[CH2:14][CH2:13]2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 787HydroxylamineHCID 59263018HCID 59263018, compound

Product 1

HCID 72264651HCID 72264651, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

To a dimethylsulfoxide (43 mL) suspension of 4.27 g of 4-{3-[1-(3-hydroxypropyl)-4-piperidinyl]propoxy}benzonitrile was added 4.32 mL of a 50% hydroxylamine aqueous solution at room temperature, which was then stirred at 40 to 50° C. for 3 hours and 30 minutes. The reaction mixture was cooled down to room temperature, to which 50 mL of water was then added dropwise over a period of 10 minutes, followed by stirring at room temperature for 30 minutes. The precipitate was collected by filtration and washed with water to provide 4.59 g of N′-hydroxy-4-{3-[1-(3-hydroxypropyl)-4-piperidinyl]propoxy}benzamidine as white solid form.

Workup

  1. additionwas then added dropwise over a period of 10 minutes
  2. stirringby stirring at room temperature for 30 minutes
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-471071fffce543a1a3f831d0fca83ff9
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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