Succinic Acid → N-Cyclopentadecyl-N-(3-pyridylmethyl)amine, succinate salt

HRID 1492333Notes

Reaction equation

HRID 1492333 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[CH:9]1([NH:24][CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>CO>[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[CH:9]1([NH:24][CH2:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 1110Succinic Acid2×HCID 14800148N-Cyclopentadecyl-N-(3-pyridylmethyl)amine

Product 1

HCID 14800149N-Cyclopentadecyl-N-(3-pyridylmethyl)amine, succinate salt

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Succinic acid (885 mg) is dissolved in methanol (10 ml). A solution of the title compound from Example 65 (950 mg) in methanol (5 ml) is added to the succinic acid solution in one portion. The solution is stirred at 20°-25° for 45 minutes and then the methanol is partially removed by evaporation at a reduced pressure. Next, ether is added to the partially evaporated solution and a white precipitate forms. The solid is collected by filtration. The solid is recrystallized from acetonitrile twice to yield the title compound, mp 148°-149° C. (PLA2, diabetes-)

Workup

  1. customthe methanol is partially removed by evaporation at a reduced pressure
  2. additionNext, ether is added to the partially evaporated solution
  3. filtrationThe solid is collected by filtration
  4. customThe solid is recrystallized from acetonitrile twice

Sources & evidence

ORD record
ord-0f36ac8d18e14f3ea3533a3e302f961f
Source dataset
uspto-grants-1994_12
Patent number
US05373095

Reaction notes

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