Ethyl Acetate → Sertraline Hydrochloride

HRID 6378

반응식

HRID 6378 반응식
C(OCC)(=O)C.[CH3:7][NH:8][C@@H:9]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C@H:12]([C:19]2[CH:20]=[CH:21][C:22]([Cl:26])=[C:23]([Cl:25])[CH:24]=2)[CH2:11][CH2:10]1.C([O-])(=O)C(C1C=CC=CC=1)O.C(=O)(O)[O-].[Na+]>O>[CH3:7][NH:8][C@@H:9]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[C@H:12]([C:19]2[CH:20]=[CH:21][C:22]([Cl:26])=[C:23]([Cl:25])[CH:24]=2)[CH2:11][CH2:10]1.[ClH:25]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 516892Sodium Bicarbonate2회HCID 131718189(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine;2-hydroxy-2-phenylacetate

생성물 1

HCID 63009Sertraline Hydrochloride

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

To a 12 liter, 3 neck round-bottom flask equipped with mechanical stirrer, 2900ml of ethyl acetate, 2900ml water and 446.1gms of sertraline mandelate salt were combined. Sodium bicarbonate, 107 grams and 3560ml of saturated sodium bicarbonate solution were then added and the resulting two essentially clear layers were separated. The aqueous layer was further extracted with 4×740ml of ethyl acetate. The combined ethyl acetate layers were washed with 3×750ml water, 900ml of brine and separated. The ethyl acetate solution was atmospherically distilled and displaced with hexanes to a final volume of 2700ml. The solution was cooled to 50° C. and seeded with sertraline hydrochloride. Concentrated hydrochloric acid, 89.2ml, was added to the clear solution to give a thick white slurry. The mixture was then cooled, stirred overnight and filtered to yield desired crystalline polymorph (Form I).

후처리

  1. customTo a 12 liter, 3 neck round-bottom flask equipped with mechanical stirrer
  2. customthe resulting two essentially clear layers were separated
  3. extractionThe aqueous layer was further extracted with 4×740ml of ethyl acetate
  4. washThe combined ethyl acetate layers were washed with 3×750ml water, 900ml of brine
  5. customseparated
  6. distillationThe ethyl acetate solution was atmospherically distilled
  7. additionConcentrated hydrochloric acid, 89.2ml, was added to the clear solution
  8. customto give a thick white slurry
  9. temperatureThe mixture was then cooled
  10. filtrationfiltered
  11. customto yield desired crystalline polymorph (Form I)

출처 및 근거

ORD 기록
ord-e5eb6ae685c847db85e110fce8e7fc19
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05248699

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