Réaction #2358511

ord-3bd21945be9448d69602088c0f79a153

Équation de réaction

CS(=O)(=O)c1cc(F)cc(OCCBr)c1
1-(2-bromoethoxy)-3-fluoro-5-methylsulfonyl-benzene
NC1CCCC1
cyclopentylamine
CS(=O)(=O)c1cc(F)cc(OCCNC2CCCC2)c1
title compound
Rendement 87.5%
CS(=O)(=O)c1cc(F)cc(OCCNC2CCCC2)c1
N-[2-(3-fluoro-5-methylsulfonyl-phenoxy)ethyl]cyclopentanamine
Rendement 87.5%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutrePreparation
  2. 2
    AutrePurification by flash column chromatography (ethyl acetate/methanol, 100:0 to 85:15)

Mode opératoire

Preparation according to Example 1 but performed in one portion: 1-(2-bromoethoxy)-3-fluoro-5-methylsulfonyl-benzene (0.5 g, 1.68 mmol) and cyclopentylamine (1.34 ml, 13.46 mmol) in ethanol (5 ml). Purification by flash column chromatography (ethyl acetate/methanol, 100:0 to 85:15) gave the title compound (443 mg, 87.4%). The amine was converted to the hydrochloric acid salt and re-crystallized from methanol/diethyl ether: M.p. 207.5° C. MS m/z (relative intensity, 70 eV) 301(M+, 2), 272 (7), 99 (24), 98 (bp), 70 (7).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09120728B2uspto-grants-2015_09