HCID 11556693, compound → HCID 11166098, compound

HRID 350823Notes

Reaction equation

HRID 350823 reaction equation
C1(S(O)(=O)=O)C2C=CC=C(S(O)(=O)=O)C=2C=CC=1.[CH3:19][NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:29]1[CH2:33][CH2:32][C@@H:31]([C:34]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:35]([NH2:37])=[O:36])[CH2:30]1>C(O)(C)C>[CH3:19][NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:29]1[CH2:33][CH2:32][C@@H:31]([C:34]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:35]([NH2:37])=[O:36])[CH2:30]1

Participants

3

Reactant 1

HCID 11556693HCID 11556693, compound

Product 1

HCID 11166098HCID 11166098, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

To an 1 L flask was added 2-[(S)-1-(8-methylaminooctyl)pyrrolidin-3-yl]-2,2-diphenylacetamide naphthalene-1,5-disulfonic acid salt (21.4 g, 30.1 mmol) and isopropanol containing 3% water by volume (637 mL). The resulting slurry was stirred at 80° C. for 2 hours and then slowly cooled to room temperature and then stirred at room temperature for 12 hours. The resulting crystalline salt was filtrated, washed with isopropanol (600 mL) and then dried under vacuum and nitrogen for 16 hours at room temperature to give the title compound as a white, crystalline solid (20.4 g, 96% yield).

Workup

  1. temperatureslowly cooled to room temperature
  2. stirringstirred at room temperature for 12 hours
  3. filtrationThe resulting crystalline salt was filtrated
  4. washwashed with isopropanol (600 mL)
  5. customdried under vacuum and nitrogen for 16 hours at room temperature

Sources & evidence

ORD record
ord-b6f842bbba8a44c296c18b3fecb38fc4
Source dataset
uspto-grants-2007_02
Patent number
US07183292B2

Reaction notes

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