Potassium Iodide → 4-{4-[(1-isopropylazetidin-3-yl)methoxy]phenyl}tetrahydro-2H-pyran-4-carbonitrile

HRID 273078노트

반응식

HRID 273078 반응식
Cl.Cl[CH2:3][CH:4]1[CH2:7][N:6]([CH:8]([CH3:10])[CH3:9])[CH2:5]1.[OH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2([C:24]#[N:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[CH:8]([N:6]1[CH2:7][CH:4]([CH2:3][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3([C:24]#[N:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:14][CH:13]=2)[CH2:5]1)([CH3:10])[CH3:9]

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 230916094-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrileHCID 685790653-(Chloromethyl)-1-isopropylazetidine hydrochloride

생성물 1

HCID 598374014-{4-[(1-isopropylazetidin-3-yl)methoxy]phenyl}tetrahydro-2H-pyran-4-carbonitrile수율 60.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3-(chloromethyl)-1-isopropylazetidine hydrochloride (2.8 g, 15.2 mmol), 4-(4-hydroxyphenyl)tetrahydropyran-4-carbonitrile (3.1 g, 15.2 mmol) and potassium carbonate (8.5 g, 61.6 mmol) were combined in DMF (40 ml) and stirred at 500 for 2 hours. Potassium iodide (0.5 g 3.0 mmol) was added and the mixture was stirred at 50° for 18 hours then at 90-95° for a further 5 hours. The reaction mixture was concentrated in vacuo then partitioned between ethyl acetate (80 ml) and water (50 ml). The ethyl acetate was washed with saturated NaCl (50 ml) then dried over Na2SO4 and concentrated in vacuo to give a brown semi-crystalline material which was triturated with diisopropyl ether (25 ml) to give the title compound as a beige powder (2.9 g, 60%). 1H NMR (400 MHz, CDCl3) δ7.38 (d, 2H), 6.91 (d, 2H), 4.08 (m, 4H), 3.89 (m, 2H), 3.41 (t, 2H), 3.02 (t, 2H), 2.87 (m, 1H), 2.31 (m, 1H), 2.15-2.00 (m, 4H), 0.94 (d, 6H).

후처리

  1. stirringthe mixture was stirred at 50° for 18 hours
  2. waitat 90-95° for a further 5 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthen partitioned between ethyl acetate (80 ml) and water (50 ml)
  5. washThe ethyl acetate was washed with saturated NaCl (50 ml)
  6. dry with materialthen dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto give a brown semi-crystalline material which
  9. customwas triturated with diisopropyl ether (25 ml)

출처 및 근거

ORD 기록
ord-5f8a5fee1a294e6689badaa9c69fa8ab
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456164B2

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