Methylparaben → 4-(2-Piperidinoethoxy)benzoic acid hydrochloride

HRID 1290037

반응식

HRID 1290037 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8]C)=[O:7])=[CH:4][CH:3]=1.Cl.[Cl:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>C(OCCCCC)(=O)C>[ClH:13].[N:16]1([CH2:15][CH2:14][O:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

참가 물질

5

반응물 3

HCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochloride

생성물 1

HCID 57438354-(2-Piperidinoethoxy)benzoic acid hydrochloride

시약·촉매·용매 1

HCID 12348Amyl Acetate용매

반응 조건

온도
125 °C

실험 절차

To a 125 mL 3 neck flask with mechanical stirring, condenser, and a heating apparatus consisting of an RTD probe in the flask hooked via a temperature controller to a heating mantle, the following were added: 7.61 g methyl 4-hydroxybenzoate, 11.05 g β-chloroethylpiperidine hydrochloride, 16.59 g powdered potassium carbonate, and 60 mL amyl acetate. The mixture was heated overnight under nitrogen in an oil bath to 125° C., and was allowed to proceed until HPLC indicated complete consumption of the methyl 4-hydroxybenzoate. The mixture was cooled to ambient temperature and 40 mL deionized water was added to dissolve the solids. The aqueous layer was separated and discarded. The water wash was repeated. 25 mL of 8N hydrochloric acid were added to extract intermediate. The layers were separated and the acid layer returned to the reaction flask. The acid solution was heated to 95° C. for about 24 hours as a "stress" test; (after 6 hours 1% of the uncleaved ester remained.) The mixture was cooled to 40° C. and 25 mL acetone added. The mixture was cooled to 0° C.-5° C. for 1 hour. The mixture was filtered and the cakes rinsed with approx. 25 mL acetone and dried. Yield=12.0 g (84.1% of theoretical).

후처리

  1. additionthe following were added
  2. customconsumption of the methyl 4-hydroxybenzoate
  3. temperatureThe mixture was cooled to ambient temperature
  4. additionwas added
  5. dissolutionto dissolve the solids
  6. customThe aqueous layer was separated
  7. washThe water wash
  8. addition25 mL of 8N hydrochloric acid were added
  9. extractionto extract intermediate
  10. customThe layers were separated
  11. temperatureThe acid solution was heated to 95° C. for about 24 hours as a "stress" test
  12. temperature(after 6 hours 1% of the uncleaved ester remained.) The mixture was cooled to 40° C.
  13. addition25 mL acetone added
  14. temperatureThe mixture was cooled to 0° C.-5° C. for 1 hour
  15. filtrationThe mixture was filtered
  16. washthe cakes rinsed with approx. 25 mL acetone
  17. customdried

출처 및 근거

ORD 기록
ord-7fc772d8c7304f1db5c2a5bbdb45b32c
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750688

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