Hydrochloric Acid → Doxepin

HRID 1894776

반응식

HRID 1894776 반응식
Cl[CH2:2][CH2:3][CH:4]=[C:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][O:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2.[CH3:20][NH:21][CH3:22].O.Cl>O1CCCC1.C(O)C>[CH3:20][N:21]([CH3:22])[CH2:2][CH2:3][CH:4]=[C:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH2:9][O:8][C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=2

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 962Water2회HCID 6706912511-(3-Chloropropylidene)-6,11-dihydrodibenzo[b,e]-oxepine

생성물 1

HCID 3158Doxepin수율 73.5%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

5.4 g (0.02 mol) of the 11-(3-chloropropylidene)-6,11-dihydrodibenzo-[b,e]-oxepine, prepared according to (c) above, in 20 mL tetrahydrofuran and 5.5 g (0.12 mol) dimethylamine in 20 mL ethanol is heated together for 3 hours using a glass autoclave and a temperature of 95-100° C. (boiling water bath). Water and 6 N hydrochloric acid are added to the contents of the autoclave and the mixture is extracted with ether. The separated, aqueous-acid components are then made alkaline with dilute caustic soda solution, and the oil thereby separated is taken up in ether. The ether residue, after distillation in a high vacuum, produces 4.1 g (73.5% of theory) of 11-(3-dimethylamino-propylidene)-6,11-dihydrodibenzo-[b,e]-oxepine, having a B.P.0.1 147-150° C. The melting point of the hydrochloride is 182-184° C. (recrystallized from isopropanol).

후처리

  1. extractionthe mixture is extracted with ether
  2. customthe oil thereby separated
  3. distillationThe ether residue, after distillation in a high vacuum

출처 및 근거

ORD 기록
ord-22cab5bdf5974c8da87fa3125ebfa127
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513299B2

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