Reaktion #58673

Reaktionsgleichung

N-[2,3-bis(4-chlorophenyl)-1-methylpropyl]-amine hydrochloride

1-(4-chlorophenyloxy)cyclohexanecarboxylic acid

N,N-diisopropylethylamine

→

title compound

N-[2,3-Bis(4-chlorophenyl)-1-methylpropyl]-1-(4-chlorophenyloxy)-cyclohexanecarboxamide

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Wascheneluted with 6:1 hexane/ether

Vorschrift

To a mixture of N-[2,3-bis(4-chlorophenyl)-1-methylpropyl]-amine hydrochloride (Diastereomer α, Reference Example 1) (60 mg, 0.19 mmol) and 1-(4-chlorophenyloxy)cyclohexanecarboxylic acid (60 mg, 0.24 mmol) in 1 mL of methylene chloride was added N,N-diisopropylethylamine (0.10 mL, 0.58 mmol) and tris(pyrrolindinyl)phosphonium hexafluorophosphate (0.10 g, 0.19 mmol). After stirring at room temperature overnight, the reaction mixture was loaded onto a silica gel column eluted with 6:1 hexane/ether to afford the title compound. 1H NMR (500 MHz, CD3OD): δ 7.22 (d, 2H), 7.19 (d, 2H), 7.03 (d, 2H), 6.99 (d, 2H), 6.91 (d, 2H), 6.71 (d, 2H), 4.24 (m, 1H), 2.99 (dd, 1H), 2.80 (ddd, 1H), 2.63 (dd, 1H), 2.3-1.2 (m, 10H), 0.82 (d, 3H). LC-MS: m/e 530 (M+H)+ (5.0 min).

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