1,5-Naphthalenedisulfonic acid → HCID 11556693, compound

HRID 2113098Notes

Reaction equation

HRID 2113098 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][C@@H:13]([C:16]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:17]([NH2:19])=[O:18])[CH2:12]1.[C:32]1([S:46]([OH:49])(=[O:48])=[O:47])[C:41]2[CH:40]=[CH:39][CH:38]=[C:37]([S:42]([OH:45])(=[O:44])=[O:43])[C:36]=2[CH:35]=[CH:34][CH:33]=1>C(O)(C)C.CCO.O>[C:32]1([S:46]([OH:49])(=[O:48])=[O:47])[C:41]2[CH:40]=[CH:39][CH:38]=[C:37]([S:42]([OH:45])(=[O:44])=[O:43])[C:36]=2[CH:35]=[CH:34][CH:33]=1.[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][C@@H:13]([C:16]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:17]([NH2:19])=[O:18])[CH2:12]1

Participants

6

Reactant 2

HCID 66661,5-Naphthalenedisulfonic acidHCID 11166098HCID 11166098, compound

Product 1

HCID 11556693HCID 11556693, compoundYield 648%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

2-[(S)-1-(8-Methylaminooctyl)pyrrolidin-3-yl]-2,2-diphenylacetamide (0.084 g, 0.2 mmol, free base) was dissolved in isopropanol (2 mL). A solution of naphthalene-1,5-disulfonic acid (0.058 g, 0.2 mmol) in a mixture of EtOH (1.7 mL) and water (0.3 mL) was added slowly and the reaction mixture was heated at 45° C. to 50° C. for about 20 minutes. The reaction mixture was then cooled slowly to room temperature at which time the solution became cloudy and then formed a white suspension. This mixture was allowed to sit overnight at ambient temperature (under a gentle stream of nitrogen). The resulting crystals were then collected by filtration and then dried to give the title compound (0.92 g, 65% yield) as a white crystalline solid.

Workup

  1. additionwas added slowly
  2. temperaturethe reaction mixture was heated at 45° C. to 50° C. for about 20 minutes
  3. customformed a white suspension
  4. filtrationThe resulting crystals were then collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-42d8e47614d14e189601e84a3ac32c87
Source dataset
uspto-grants-2009_04
Patent number
US07524880B2

Reaction notes

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