반응 #1547653

반응 방정식

(R)-3-chloro-1-(4-methoxyphenethyl)piperidine

Potassium hydride

5,11-dihydrodibenzo[b,e][1,4]thiazepine

→

title compound

수율 12.0%

(S)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepine

수율 12.0%

용매

DME

DME

반응 조건

후처리

1. 1
   온도heated
2. 2
   온도under reflux for 18 hours
3. 3
   기타quenched with water
4. 4
   추출extracted with ethyl acetate
5. 5
   세척The organic layer was washed with water
6. 6
   건조dried over sodium sulphate
7. 7
   기타evaporated under reduced pressure
8. 8
   기타The residue was purified by chromatography on silica gel
9. 9
   세척a gradient elution
10. 10
    기타evaporated under reduced pressure

실험 절차

Potassium hydride (35% dispersion in oil, 229 mg) was added to a solution of 5,11-dihydrodibenzo[b,e][1,4]thiazepine (see U.S. Pat. No. 3,188,322 [Chem. Abs., 63, 8384h (1965)] and I. Udea and S. Umio, Bull. Chem. Soc. Japan, 48(8), 2323 (1975)) (425 mg) in DME (1,2-dimethoxyethane) (20 ml) and the mixture stirred at room temperature for 30 minutes, treated with a solution of (R)-3-chloro-1-(4-methoxyphenethyl)piperidine (see Preparation 1) (507 mg) in DME (5 ml) and heated under reflux for 18 hours. The mixture was cooled to room temperature, quenched with water and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulphate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel, performing a gradient elution using initially dichloromethane as eluant and changing to dichloromethane/saturated methanolic ammonia (98:2). The appropriate fractions were combined and evaporated under reduced pressure to give the title compound as a colourless oil, (100 mg, 12%), [α]58925 -60.9° (c=0.57 in ethanol).

출처