Succinic Acid → (R)-5-(2-Ethylsulphonylethyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole hemisuccinate

HRID 744152Notes

Reaction equation

HRID 744152 reaction equation
[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[CH2:9]([S:11]([CH2:14][CH2:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[C:19]2[CH2:25][C@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[CH3:31])(=[O:13])=[O:12])[CH3:10]>C(O)C>[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[CH2:9]([S:11]([CH2:14][CH2:15][C:16]1[CH:17]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[C:19]2[CH2:25][C@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[CH3:31])(=[O:13])=[O:12])[CH3:10].[CH2:9]([S:11]([CH2:1][CH2:2][C:3]1[CH:4]=[C:18]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH:20]=[C:19]2[CH2:25][C@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[CH3:31])(=[O:13])=[O:12])[CH3:10]

Participants

4

Reactant 2

HCID 1110Succinic AcidHCID 9884122(R)-5-(2-Ethylsulphonylethyl)-3-(N-methylpyrrolidin-2-ylmethyl)1H-indole

Product 1

HCID 131719486(R)-5-(2-Ethylsulphonylethyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole hemisuccinateYield 163.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of succinic acid (69 mg) in hot ethanol (3.5 mL) was added slowly with stirring to a solution of (R)-5-(2-ethylsulphonylethyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole free base (390 mg) in ethanol (3.5 mL). The solution was evaporated and the residue was triturated first with ether and then with ethyl acetate to give the title compound as a solid (375 mg): mp 59°-62° C.: [α]25D =+36° (methanol, c=0.10) Anal Calcd for C18H26N2O2S. 0.5 C4H6O4. 0.25 CH3CO2C2H5. 0.5 H2O: C,59.00; H,7.42; H,6.68. Found: C,59.17; H,7.37; N,6.73.

Workup

  1. customThe solution was evaporated
  2. customthe residue was triturated first with ether

Sources & evidence

ORD record
ord-0cbe4f0cf15940408d1c2a8063614b2c
Source dataset
uspto-grants-1996_09
Patent number
US05559129

Reaction notes

Loading…