Potassium Carbonate → 4-[3-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-carbonitrile

HRID 272900

반응식

HRID 272900 반응식
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Cl[CH2:17][CH2:18][CH2:19][N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:20]1([CH2:19][CH2:18][CH2:17][O:1][C:2]2[CH:3]=[C:4]([C:8]3([C:14]#[N:15])[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[CH:5]=[CH:6][CH:7]=2)[CH2:24][CH2:23][CH2:22][CH2:21]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 112871604-Cyano-4-(3-hydroxyphenyl)-3,4,5,6-tetrahydro-2H-pyranHCID 113210281-(3-Chloropropyl)-pyrrolidine

생성물 1

HCID 598374824-[3-(3-Pyrrolidin-1-ylpropoxy)phenyl]tetrahydropyran-4-carbonitrile수율 31.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-(3-Hydroxy-phenyl)-tetrahydro-2H-pyran-4-carbonitrile (1.03 g, 5.10 mmol), 1-(3-chloro-propyl)-pyrrolidine (600 mg, 4.08 mmol), DMF (6.8 ml) and K2CO3 (2.82 g, 20.4 mmol) were reacted together according to general procedure E. The organic phase was washed with 2M NaOH (3×50 ml), brine (3×50 ml), dried over MgSO4, fitered and concentrated in vacuo at 35° C. The crude mixture was slurried in TBME:heptane (1:20, 10 ml). The solid was filtered, washed with heptane (10 ml) and dried on the filter for 2 hours to give the title compound (0.4 g, 31%). 1H NMR (400 MHz, CDCl3) δ 7.32 (t, 1H), 7.07-6.99 (m, 2H), 6.87 (dd, 1H), 4.11-4.04 (m, 2H), 4.05 (t, 2H), 3.90 (td, 2H), 2.63 (t, 2H), 2.57-2.49 (m, 4H), 2.18-1.97 (m, 6H), 1.84-1.75 (m, 4H).

후처리

  1. washThe organic phase was washed with 2M NaOH (3×50 ml), brine (3×50 ml)
  2. dry with materialdried over MgSO4
  3. concentrationfitered and concentrated in vacuo at 35° C
  4. filtrationThe solid was filtered
  5. washwashed with heptane (10 ml)
  6. customdried on the
  7. filtrationfilter for 2 hours

출처 및 근거

ORD 기록
ord-974f952d1fee4b1e95f6200d1092d00b
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456164B2

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