Hydrochloric Acid → T-2307

HRID 644138Notes

Reaction equation

HRID 644138 reaction equation
[OH2:1].[NH2:2][C:3](=[NH:33])[C:4]1[CH:32]=[CH:31][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][O:21][C:22]3[CH:30]=[CH:29][C:25]([C:26]([NH2:28])=[NH:27])=[CH:24][CH:23]=3)[CH2:14][CH2:13]2)=[CH:6][CH:5]=1.[ClH:34]>CC(O)C>[OH2:8].[OH2:1].[OH2:8].[OH2:8].[OH2:8].[ClH:34].[ClH:34].[ClH:34].[NH2:33][C:3](=[NH:2])[C:4]1[CH:32]=[CH:31][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][O:21][C:22]3[CH:23]=[CH:24][C:25]([C:26]([NH2:28])=[NH:27])=[CH:29][CH:30]=3)[CH2:14][CH2:13]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 9803135T-2307 free base

Product 1

HCID 66920461T-2307

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
60 °C

Procedure

To a water (40 mL)/2-propanol (80 mL) suspension of 20.0 g of 4-{3-[4-(3-{4-[amino(imino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamidine was added 14.3 g of hydrochloric acid, which was then stirred at 60° C. for 10 minutes. Thereto was added 120 mL of 2-propanol, to which 100 mg of seed crystals were added, followed by stirring at room temperature for 35 minutes and under cooling with ice for 2 hours. The precipitated crystals were collected by filtration to provide 28.3 g of 4-{3-[4-(3-{4-[amino(imino)methyl]phenoxy}propyl)-1-piperidinyl]propoxy}benzamidine trihydrochloride pentahydrate as colorless crystals.

Workup

  1. additionto which 100 mg of seed crystals were added
  2. stirringby stirring at room temperature for 35 minutes
  3. temperatureunder cooling with ice for 2 hours
  4. filtrationThe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-645644d6f0a94dc0acb0aaadb2f51ba8
Source dataset
uspto-grants-2010_04
Patent number
US07700623B2

Reaction notes

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