Piperidine → 1-[3-[3-(Trifluoromethyl)phenoxy]-1-azetidinylcarbonyl]piperidine

HRID 974597

반응식

HRID 974597 반응식
Cl[C:2]([N:4]1[CH2:7][CH:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[CH2:5]1)=[O:3].C(=O)([O-])[O-].[K+].[K+].[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>O1CCCC1.C1C=CC=CC=1>[F:16][C:15]([F:18])([F:17])[C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][CH:12]=1)[O:8][CH:6]1[CH2:7][N:4]([C:2]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:3])[CH2:5]1

참가 물질

6

반응물 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 197996061-Chlorocarbonyl-3-[3-(trifluoromethyl)phenoxy]azetidine

생성물 1

HCID 150533901-[3-[3-(Trifluoromethyl)phenoxy]-1-azetidinylcarbonyl]piperidine

시약·촉매·용매 2

HCID 241Benzene용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-70 °C

실험 절차

A solution of 5.6 g (0.02 mole) of 1-chlorocarbonyl-3-[3-(trifluoromethyl)phenoxy]azetidine in 50 ml of tetrahydrofuran was treated with 3 g (0.022 mole) of potassium carbonate and while stirring, 1.9 g (0.022 mole) of piperidine was added dropwise. The mixture was then treated with 10 g of ice and stirred for 2 hr. The tetrahydrofuran was decanted then concentrated on a rotary evaporator to yield an amber oil, 6.0 g. The oil was dissolved in benzene, washed with dilute acid then water, dried over magnesium sulfate and concentrated in vacuo. This oil crystallized when cooled to -70° C. and was recrystallized from hexane with charcoal treatment at 0° C. yielding pale tan crystals, 4.5 g (68.5%), m.p. 50°-52° C.

후처리

  1. stirringstirred for 2 hr
  2. customThe tetrahydrofuran was decanted
  3. concentrationthen concentrated on a rotary evaporator
  4. customto yield an amber oil, 6.0 g
  5. washwashed
  6. additionwith dilute acid
  7. dry with materialwater, dried over magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThis oil crystallized when
  10. customwas recrystallized from hexane with charcoal treatment at 0° C.
  11. customyielding pale tan crystals, 4.5 g (68.5%), m.p. 50°-52° C.

출처 및 근거

ORD 기록
ord-7b1896573f7d4ba6a0a5bb624f7954e5
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05068231

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