Potassium Carbonate → 4-{4-[2-(1-Methylpyrrolidin-2-yl)ethoxy]phenyl}tetrahydro-pyran-4-carbonitrile

HRID 272916

반응식

HRID 272916 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.Cl[CH2:17][CH2:18][CH:19]1[CH2:23][CH2:22][CH2:21][N:20]1[CH3:24].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:24][N:20]1[CH2:21][CH2:22][CH2:23][CH:19]1[CH2:18][CH2:17][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 2850932-(2-Chloroethyl)-1-methylpyrrolidineHCID 230916094-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile

생성물 1

HCID 598373854-{4-[2-(1-Methylpyrrolidin-2-yl)ethoxy]phenyl}tetrahydro-pyran-4-carbonitrile수율 15%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrile (1.0 g, 4.9 mmol), 2-(2-chloro-ethyl)-1-methyl-pyrrolidine (722 mg, 3.90 mmol), DMF (20 ml) and K2CO3 (2.71 g, 19.60 mmol) were reacted together according to general procedure E. The organic phase was washed with 2M NaOH (3×20 ml), water (2×20 ml), dried over MgSO4, fitered and concentrated in vacuo at 35° C. and purified by prep TLC, eluting with DCM:MeOH:NH3 (95:5:3), to provide the title compound (180 mg, 15%) as a yellow oil. 1H NMR (400 MHz, CDCl3), δ 7.38 (d, 2H), 6.93 (d, 2H), 4.12-4.03 (m, 4H), 3.89 (td, 2H), 3.08 (m, 1H), 2.35 (s, 3H), 2.29-1.94 (m, 8H), 1.85-1.65 (m, 2H), 1.62-1.50 (m, 2H).

후처리

  1. washThe organic phase was washed with 2M NaOH (3×20 ml), water (2×20 ml)
  2. dry with materialdried over MgSO4
  3. concentrationfitered and concentrated in vacuo at 35° C.
  4. custompurified by prep TLC
  5. washeluting with DCM:MeOH:NH3 (95:5:3)

출처 및 근거

ORD 기록
ord-5715f67e66d746959f3dac0a72bf0d79
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456164B2

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