Ethanol → (R)-5-(2-Benzenesulphonylethyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole hemisuccinate

HRID 745013Notes

Reaction equation

[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[C:9]1([S:15]([CH2:18][CH2:19][C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[NH:25][CH:24]=[C:23]3[CH2:29][C@H:30]2[CH2:34][CH2:33][CH2:32][N:31]2[CH3:35])(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(O)C>>[C:1]([OH:8])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].[C:9]1([S:15]([CH2:18][CH2:19][C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[NH:25][CH:24]=[C:23]3[CH2:29][C@H:30]2[CH2:34][CH2:33][CH2:32][N:31]2[CH3:35])(=[O:17])=[O:16])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1.[C:9]1([S:15]([CH2:18][CH2:19][C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[NH:25][CH:24]=[C:23]3[CH2:29][C@H:30]2[CH2:34][CH2:33][CH2:32][N:31]2[CH3:35])(=[O:17])=[O:16])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Reactant 3

HCID 702Ethanol2×

HCID 1110Succinic Acid

HCID 77993Eletriptan

Product 1

HCID 131719487(R)-5-(2-Benzenesulphonylethyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole hemisuccinateYield 95.7%

Procedure

A solution of succinic acid (95 mg) in ethanol (5 mL) was added to a solution of (R)-5-(2-benzenesulphonylethyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole free base (620 mg) in ethanol (5 mL). The solution was evaporated to give the title compound as a foam (680 mg): [α]25D =+29° (methanol, c=0.10). Anal. Calcd for C22H26N2O2S. 0.5 C4H6O4. 0.33 C2H5OH. 0.5 H2O; C,63.59; H,6.9.2; N,6.01. Found: C,63.52; H,6.91; N,6.12.

Workup

customThe solution was evaporated

Sources & evidence

ORD record: ord-3e0ec51e8f6f4c5ab8554d86d89524e1
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05559246

Reaction notes

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