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

HRID 1077866Notes

Reaction equation

HRID 1077866 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-9fdcebd5d2654314840a76d6c382b5ac
Source dataset
uspto-grants-1996_08
Patent number
US05545644

Reaction notes

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