Hydrochloric Acid → Tamsulosin Hydrochloride

HRID 1294092

반응식

HRID 1294092 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=O)[CH3:11])=[CH:5][C:4]=1[S:13]([NH2:16])(=[O:15])=[O:14].[CH2:17]([O:19][C:20]1[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=1[O:22][CH2:23][CH2:24][NH2:25])[CH3:18].[H][H].[ClH:32]>[Ni].CO>[CH3:18][CH2:17][O:19][C:20]1[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=1[O:22][CH2:23][CH2:24][NH:25][C@@H:10]([CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([S:13]([NH2:16])(=[O:15])=[O:14])[CH:5]=1)[CH3:11].[ClH:32]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 53030422-(2-Ethoxyphenoxy)ethylamineHCID 141797592-Methoxy-5-(2-oxopropyl)benzenesulfonamideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 5362376Tamsulosin Hydrochloride

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

실험 절차

2-Methoxy-5-(2-oxopropyl)-benzene sulfonamide (37.3 gm, 153.3 mmol), 2-(2-ethoxyphenoxy)-1-ethanamine (29.8 gm, 164.4 mmol) and methanol (250 mL) were taken into a one liter stainless steel flask and mixed well. Catalyst Raney nickel (8 gm) was added to the flask and the mixture hydrogenated at 50° C. at hydrogen pressure of 40 psi for 30 hrs. The catalyst was removed by filtration and solvent from the filtrate was distilled off completely at 50° C. under vacuum. The dark brown crude obtained was treated with methanolic hydrochloric acid (175 mL) at 0-5° C. under stirring. Tamsulosin hydrochloride formed as a solid was filtered, washed with ethyl acetate (200 mL), suspended in methanol (120 mL) and the methanol slurry filtered to obtain off white solid material. It was dried for 3 hrs at 80° C. to give racemic tamsulosin hydrochloride. Melting point 255-257° C., chemical purity of 98.8 area % (by HPLC) and R,S ratio of 51.45:48.55 (by chiral HPLC).

후처리

  1. additionmixed well
  2. customThe catalyst was removed by filtration and solvent from the filtrate
  3. distillationwas distilled off completely at 50° C. under vacuum
  4. customThe dark brown crude obtained

출처 및 근거

ORD 기록
ord-24a195faf6134ca3b1d534f14ef3f498
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238839B2

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