Acetic Anhydride → 4-{3-[1-(3-Hydroxypropyl)-4-piperidinyl]propoxy}benzamidine

HRID 644132Notes

Reaction equation

HRID 644132 reaction equation
O[N:2]=[C:3]([NH2:24])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][CH2:13][CH:14]2[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH2:22][OH:23])[CH2:16][CH2:15]2)=[CH:6][CH:5]=1.C(OC(=O)C)(=O)C>[C].[Pd].C(O)(=O)C>[OH:23][CH2:22][CH2:21][CH2:20][N:17]1[CH2:16][CH2:15][CH:14]([CH2:13][CH2:12][CH2:11][O:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([NH2:24])=[NH:2])=[CH:9][CH:8]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 72264651HCID 72264651, compound

Product 1

HCID 592630244-{3-[1-(3-Hydroxypropyl)-4-piperidinyl]propoxy}benzamidineYield 110.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

To an acetic acid (50 mL) suspension of 4.58 g of N′-hydroxy-4-{3-[1-(3-hydroxypropyl)-4-piperidinyl]propoxy}benzamidine was added 2.59 mL of acetic anhydride at room temperature, which was then stirred at the same temperature for one hour. To the reaction mixture was added 0.50 g of 5% palladium-carbon, which was then stirred at room temperature under hydrogen atmosphere for 5 hours and 30 minutes. Insoluble matter was filtered off, and the solvent was distilled off under reduced pressure. Water was added to the resultant residue, which was adjusted to pH 12.5 using a 5 mol/L sodium hydroxide aqueous solution. The precipitate was collected by filtration and washed with water to provide 4.82 g of 4-{3-[1-(3-hydroxypropyl)-4-piperidinyl]propoxy}benzamidine as white solid form.

Workup

  1. stirringwas then stirred at room temperature under hydrogen atmosphere for 5 hours and 30 minutes
  2. filtrationInsoluble matter was filtered off
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionWater was added to the resultant residue, which
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-84cdd42af55f4c7cab81c10fe172d279
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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