Water → HCID 178457602, compound

HRID 229348Notes

Reaction equation

HRID 229348 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[F:9][C:10]([F:34])([F:33])[O:11][C:12]1[CH:32]=[CH:31][C:15]([O:16][CH2:17][CH2:18][CH2:19][O:20][NH:21][C:22]([NH:24][C:25]([NH:27][CH:28]([CH3:30])[CH3:29])=[NH:26])=[NH:23])=[CH:14][CH:13]=1.O>C(O)C>[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[F:9][C:10]([F:33])([F:34])[O:11][C:12]1[CH:13]=[CH:14][C:15]([O:16][CH2:17][CH2:18][CH2:19][O:20][NH:21][C:22]([NH:24][C:25]([NH:27][CH:28]([CH3:29])[CH3:30])=[NH:26])=[NH:23])=[CH:31][CH:32]=1.[F:9][C:10]([F:33])([F:34])[O:11][C:12]1[CH:13]=[CH:14][C:15]([O:16][CH2:17][CH2:18][CH2:19][O:20][NH:21][C:22]([NH:24][C:25]([NH:27][CH:28]([CH3:29])[CH3:30])=[NH:26])=[NH:23])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1110Succinic AcidHCID 178457601HCID 178457601, compound

Product 1

HCID 178457602HCID 178457602, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Succinic acid (1.05 g, 8.9 mmol) was added to a solution of 1-(3-(4-trifluoromethoxyphenoxy)propyloxy)-5-isopropyl biguanide free base (6.6 grams, 17.5 mmol) in 20 ml of ethanol. The mixture was heated to dissolve the acid and water (40 ml) was added. The solution was cooled to room temperature and subsequently refrigerated to complete crystallization. The crystals were isolated by filtration, washed with 5 ml of ice-cold 50% ethanol and dried to yield 1-(3-(4-trifluoromethoxyphenoxy)propyloxy)-5-isopropyl biguanide hemisuccinate (6.0 grams 78.5%), with melting point 154° C.-155° C. Elemental Analysis for C17H25N5O5ClF3: Calculated: C, 46.78; H, 5.77; N, 16.04. Found: C, 46.85; H, 5.78; N, 15.86.

Workup

  1. temperatureThe mixture was heated
  2. additionwas added
  3. customcrystallization
  4. customThe crystals were isolated by filtration
  5. washwashed with 5 ml of ice-cold 50% ethanol
  6. customdried

Sources & evidence

ORD record
ord-e3a93918a5144d46947940934dac5ca8
Source dataset
uspto-grants-2009_07
Patent number
US07563792B2

Reaction notes

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