Reaktion #1519144

ord-70ed7edf20a14dcc83a1c3858fce7214

Reaktionsgleichung

N[C@H]1c2ccccc2C[C@H]1O
(1S,2R)-1-aminoindan-2-ol
CCN(CC)CC
triethylamine
Cc1ccc(S(=O)(=O)N(CCCl)CCCl)cc1
N,N-bis(2-chloroethyl)-p-toluenesulphonamide
Cc1ccc(S(=O)(=O)N2CCN([C@H]3c4ccccc4C[C@H]3O)CC2)cc1
expected product
Cc1ccc(S(=O)(=O)N2CCN([C@H]3c4ccccc4C[C@H]3O)CC2)cc1
(1S,2R)-1-{4-[(4-Methylphenyl)sulphonyl]piperazin-1-yl}indan-2-ol

Lösungsmittel

Reaktionsbedingungen

Temperatur
80°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe dimethylformamide is evaporated off
  2. 2
    Waschenwashed
  3. 3
    Sonstigedried
  4. 4
    Filtrationfiltered
  5. 5
    Sonstigeevaporated
  6. 6
    SonstigeThe oil obtained
  7. 7
    Sonstigeis purified by flash chromatography on silica (eluant: dichloromethane/ethyl acetate 95/5)

Vorschrift

To 8 g of (1S,2R)-1-aminoindan-2-ol (53.6 mmol) dissolved in 80 ml of dimethyl-formamide there are added 15 ml of triethylamine (107.2 mmol) and 15.8 g of N,N-bis(2-chloroethyl)-p-toluenesulphonamide (53.6 mmol). The mixture is heated at 80° C. for 24 hours and then the dimethylformamide is evaporated off. The residue is taken up in dichloromethane, washed, dried, filtered and evaporated. The oil obtained is purified by flash chromatography on silica (eluant: dichloromethane/ethyl acetate 95/5) to yield the expected product in the form of a meringue.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07612061B2uspto-grants-2009_11