Water → HCID 178457602, compound

HRID 853922Notes

Reaction equation

HRID 853922 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-914a77d8a15d449e86472f7bb2279ffe
Source dataset
uspto-grants-2007_08
Patent number
US07256218B2

Reaction notes

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