Potassium Hydroxide → 1-Carbethoxy-4-methylamino-3-ethylpiperidine

HRID 1865233노트

반응식

HRID 1865233 반응식
Cl.CN.[C:4]([N:9]1[CH2:14][CH2:13][C:12](=O)[CH:11]([CH2:16][CH3:17])[CH2:10]1)([O:6][CH2:7][CH3:8])=[O:5].[OH-].[K+].[C:20]([BH3-])#[N:21].[Na+]>CO>[C:4]([N:9]1[CH2:14][CH2:13][CH:12]([NH:21][CH3:20])[CH:11]([CH2:16][CH3:17])[CH2:10]1)([O:6][CH2:7][CH3:8])=[O:5]

참가 물질

6

반응물 4

HCID 14797Potassium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 222788511-Carbethoxy-3-ethyl-4-piperidone

생성물 1

HCID 222788831-Carbethoxy-4-methylamino-3-ethylpiperidine

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

Methylamine hydrochloride (17 g, 252 mmol) was added to the stirred solution of 1-carbethoxy-3-ethyl-4-piperidone (10 g, 50 mmol) in methanol (150 ml) followed by 14.1 g (252 mmol) KOH. Stirring was continued for 3 hr at ambient temperature. The resulting mixture was cooled at 0° C. and sodium cyanoborohydride (4.72 g, 75 mmol) was added to it. Cooling was removed after 10 min. and resulting mixture was stirred for 12 hr at ambient temperature. The reaction mixture was concentrated to dryness, triturated with water, acidified with conc. HCl (pH 3˜4) and extracted with ethyl acetate to remove impurities. The aqueous layer was basified with 1 M sodium hydroxide solution (pH˜10) and extracted with ethyl acetate. Ethyl acetate extract was dried (Na2SO4) and concentrated to dryness to give crude 1-carbethoxy-4-methylamino-3-ethylpiperidine. The obtained crude 1-carbethoxy-4-methylamino-3-ethylpiperidine was suspended in 7 M NaOH solution (50 ml), stirred at 110° C. for 230 hr, cooled, extracted with ethyl acetate, dried (Na2SO4) and concentrated to dryness to afford 4-methylamino-3-ethyl-piperidine. Yield 3.5 g (50%), C8H18N2, m/z 142 (M+1).

후처리

  1. temperatureCooling
  2. customwas removed after 10 min.
  3. customresulting mixture
  4. stirringwas stirred for 12 hr at ambient temperature
  5. concentrationThe reaction mixture was concentrated to dryness
  6. customtriturated with water
  7. extractionextracted with ethyl acetate
  8. customto remove impurities
  9. extractionextracted with ethyl acetate
  10. extractionEthyl acetate extract
  11. dry with materialwas dried (Na2SO4)
  12. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-aaeb46f62e9e4a0cb0f4c785943c25d7
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07626032B2

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