Potassium Carbonate → 4-{3-[4-(4-Cyanotetrahydropyran-4-yl)-phenoxy]propyl}-piperazine-1-carboxylic acid ethyl ester

HRID 272907ノート

反応式

HRID 272907 の反応式
[N:1]1([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:22]#[N:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:24]([O:26][C:27]([N:29]1CCN(CCCCl)CC1)=[O:28])[CH3:25].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:24]([O:26][C:27]([N:29]1[CH2:4][CH2:5][N:1]([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3([C:22]#[N:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[CH2:2][CH2:3]1)=[O:28])[CH3:25]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 410641Ethyl 4-(3-chloropropyl)piperazine-1-carboxylateHCID 598373944-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile

生成物 1

HCID 598374324-{3-[4-(4-Cyanotetrahydropyran-4-yl)-phenoxy]propyl}-piperazine-1-carboxylic acid ethyl ester収率 28.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-carbonitrile (500 mg, 2.46 mmol), 4-(3-chloro-propyl)-piperazine-1-carboxylic acid ethyl ester (570 mg, 2.43 mmol), DMF (10 ml) and K2CO3 (1.36 g, 9.84 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. The crude product was subjected to chromatography on silica eluting with DCM:MeOH:NH3 (97:2:1) to provide the title compound (280 mg, 28%) as an off white solid. 1H NMR (400 MHz, CDCl3), δ 7.38 (d, 2H), 6.93 (d, 2H), 4.14 (q, 2H), 4.11-4.05 (m, 2H), 4.03 (t, 2H), 3.89 (td, 2H), 3.55-3.42 (m, 4H), 2.53 (t, 2H), 2.47-2.36 (m, 4H), 2.15-1.92 (m, 6H), 1.26 (t, 3H).

後処理

  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

出典と根拠

ORDレコード
ord-949bc005ee6341299f87ca3274f6fede
出典データセット
uspto-grants-2008_11
特許番号
US07456164B2

反応ノート

読み込み中…