Dimethyl Sulfoxide → N'-hydroxy-4-{3-[4-(3-hydroxypropyl)-1-piperidinyl]propoxy}benzamidine

HRID 644127Notes

Reaction equation

HRID 644127 reaction equation
CS(C)=O.[OH:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][N: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].CC(O)C>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][N:12]2[CH2:11][CH2:10][CH:9]([CH2:8][CH2:7][CH2:6][OH:5])[CH2:14][CH2:13]2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 787Hydroxylamine2×HCID 3776IsopropanolHCID 68434383HCID 68434383, compound

Product 1

HCID 72264642N'-hydroxy-4-{3-[4-(3-hydroxypropyl)-1-piperidinyl]propoxy}benzamidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dimethylsulfoxide (200 mL) solution of 18.7 g of 4-{3-[4-(3-hydroxypropyl)-1-piperidinyl]propoxy}benzonitrile was added 8.92 mL of a 50% hydroxylamine aqueous solution at room temperature, which was then stirred at the same temperature for 5 hours and 30 minutes. Thereto was added 8.92 mL of a 50% hydroxylamine aqueous solution at room temperature, which was stirred at the same temperature for 15 hours and 50 minutes. To the reaction mixture were added 2-propanol and water, which was then stirred at room temperature for one hour. The precipitate was collected by filtration and washed with water to provide 17.5 g of N′-hydroxy-4-{3-[4-(3-hydroxypropyl)-1-piperidinyl]propoxy}benzamidine as white solid form.

Workup

  1. stirringwhich was stirred at the same temperature for 15 hours and 50 minutes
  2. stirringwas then stirred at room temperature for one hour
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-4d04898d2a244b0283c2ab491337fb77
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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