Reaktion #49130

Reaktionsgleichung

(+)-{1-[amino(phenyl)methyl]cyclopentyl}dimethylamine

{1-[amino(phenyl)methyl]cyclopentyl}dimethylamine

2

(±)-2-(Methyloxy)-N-[2-methyl-1-phenyl-2-(1-pyrrolidinyl)butyl]-4,6-bis(trifluoromethyl)benzamide

triethylamine

2-methyl-4,6-bis(trifluoromethyl)benzoyl chloride

methyl 2,4-bis(trifluoromethyl)benzoate

→

title product

Ausbeute 36.0%

N-[[1-(Dimethylamino)cyclopentyl](phenyl)methyl]-2-methyl-4,6-bis(trifluoromethyl)benzamide

Ausbeute 36.0%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared
2. 2
   SonstigeThe volatile components were removed under reduced pressure
3. 3
   Sonstigethe residue chromatographed on silica gel
4. 4
   WaschenElution with 0-80% ethyl acetate in pentane

Vorschrift

A mixture of 2-methyl-4,6-bis(trifluoromethyl)benzoyl chloride and methyl 2,4-bis(trifluoromethyl)benzoate (approximately 0.5 mmol) prepared as described in D53 was dissolved in dry DCM (3 ml) and treated with (+)-{1-[amino(phenyl)methyl]cyclopentyl}dimethylamine D3 enantiomer 2 (109 mg, 0.50 mmol) and triethylamine (140 ul, 1.00 mmol) and left overnight at room temperature. The volatile components were removed under reduced pressure and the residue chromatographed on silica gel. Elution with 0-80% ethyl acetate in pentane gave the title product (86 mg, ca.36%). 1H NMR (CDCl3) δ: 0.95 (1H, br m), 1.44-1.86 (7H, overlapping m), 2.20 (6H, s), 2.41 (3H, br s), 5.10 (1H, d, J=5.6 Hz), 7.07 (1H, br s), 7.26-7.42 (5H, overlapping m), 7.67 (1H, s), 7.77 (1H, s). Mass Spectrum (Electrospray LC/MS): Found 473 (MH+) C24H26F6N2O requires 472. Ret time 2.25 min.

Quelle