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

HRID 272916

反応式

HRID 272916 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

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.
  4. custompurified by prep TLC
  5. washeluting with DCM:MeOH:NH3 (95:5:3)

出典と根拠

ORDレコード
ord-5715f67e66d746959f3dac0a72bf0d79
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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