Hydrochloric Acid → 4-{3-[4-(3-{4-[Amino(hydroxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamidine

HRID 644147Notes

Reaction equation

HRID 644147 reaction equation
[NH2:1][C:2](=[N:33]C(=O)[O-])[C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([NH2:32])=[N:30][OH:31])=[CH:25][CH:24]=3)[CH2:15][CH2:14]2)=[CH:5][CH:4]=1.Cl>C(O)C>[NH2:32][C:29](=[N:30][OH:31])[C:26]1[CH:27]=[CH:28][C:23]([O:22][CH2:21][CH2:20][CH2:19][CH:16]2[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][CH2:10][O:9][C:6]3[CH:5]=[CH:4][C:3]([C:2]([NH2:33])=[NH:1])=[CH:8][CH:7]=3)[CH2:14][CH2:15]2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86625850HCID 86625850, compound

Product 1

HCID 722646624-{3-[4-(3-{4-[Amino(hydroxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol (5 mL) suspension of 0.30 g of tert-butyl=[1-amino-1-(4-{3-[4-(3-{4-[amino(hydroxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}phenyl)methylidene]carbamate was added 5 mL of hydrochloric acid at room temperature, which was then stirred at the same temperature for 15 hours. The solvent was distilled off under reduced pressure, and water was subsequently added to the resultant residue, which was then adjusted to pH 12.5 using a 1 mol/L sodium hydroxide aqueous solution. The precipitate was collected by filtration and washed with water to provide 0.22 g of 4-{3-[4-(3-{4-[amino(hydroxyimino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamidine as white solid form.

Workup

  1. distillationThe solvent was distilled off under reduced pressure, and water
  2. additionwas subsequently added to the resultant residue, which
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-f6df706436774e76a1aa8f1bfef14749
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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