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

HRID 272900

反応式

HRID 272900 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-974f952d1fee4b1e95f6200d1092d00b
出典データセット
uspto-grants-2008_11
特許番号
US07456164B2

関連ノート

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