(1S)-(+)-Camphor-10-sulphonic acid → (-)-(6-methoxy-indan-1-yl)piperazine (1S)-10-camphorsulfonic acid salt

HRID 1956151Notes

Reaction equation

HRID 1956151 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:5][CH:4]=1.[C@:18]12([CH2:28][S:29]([OH:32])(=[O:31])=[O:30])[C:25]([CH3:27])([CH3:26])[CH:22]([CH2:23][CH2:24]1)[CH2:21][C:19]2=[O:20]>>[C@:18]12([CH2:28][S:29]([OH:32])(=[O:30])=[O:31])[C:25]([CH3:27])([CH3:26])[CH:22]([CH2:23][CH2:24]1)[CH2:21][C:19]2=[O:20].[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[N:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 218580(1S)-(+)-Camphor-10-sulphonic acidHCID 22038119(6-Methoxy-indan-1-yl)piperazine

Product 1

HCID 86752901(-)-(6-methoxy-indan-1-yl)piperazine (1S)-10-camphorsulfonic acid saltYield 22%

Procedure

A mixture of (6-methoxy-indan-1-yl)piperazine (2.3 g, 10 mmol) and (1S)-(+)-10-camphorsulfonic acid (2.3 g, 10 mmol) was recrystallized from ethanol-water until the crystal attained a constant melting point yielding (-)-(6-methoxy-indan-1-yl)piperazine (1S)-10-camphorsulfonic acid salt (22%, mp: 234.5°-234° C., [α]25D -36.3°). Calc'd for C14H20N2O2.C10 H10O4S: C, 62.04%; H, 7.81%; N, 6.03%. Found: C, 62.01%; H, 7.96; N, 5.97%.

Workup

  1. customwas recrystallized from ethanol-water until the crystal

Sources & evidence

ORD record
ord-f61b162cbfc14f849d491b5648e37fda
Source dataset
uspto-grants-1998_07
Patent number
US05780470

Reaction notes

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