Water → 4-(2-Methylpiperidin-1-YL)-3-(trifluoromethyl)benzonitrile

HRID 400734

反応式

HRID 400734 の反応式
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].[CH3:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][NH:16]1.CCOCC.O>CS(C)=O>[CH3:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][N:16]1[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11]

参加物

6

反応物 4

HCID 962WaterHCID 3283Diethyl EtherHCID 79742-MethylpiperidineHCID 1442554-Fluoro-3-(trifluoromethyl)benzonitrile

生成物 1

HCID 585541304-(2-Methylpiperidin-1-YL)-3-(trifluoromethyl)benzonitrile

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

4-fluoro-3-(trifluoromethyl)benzonitrile (Combi-blocks, 50 g; 264.40 mmol) and 2-methylpiperidine (Acros, 156.08 mL; 1 321.98 mmol) in DMSO (500 mL) were heated at 100° C. under nitrogen for 12 h. After this time, Et2O and water were added to the reaction mixture and organic phase was washed with water, NaHCO3 and a saturated aqueous solution of NH4Cl successively. Organics were dried over MgSO4, evaporated under vacuum to give the title compound as a beige powder. 1H NMR (DMSO-d6) δ 8.19 (d, J=2 Hz, 1H), 8.12 (dd, J=8.4, 2 Hz, 1H), 7.75 (d, J=8.2 Hz, 1H), 3.15-3.10 (m, 1H), 2.90-2.85 (m, 1H), 2.60-2.51 (m, 1H), 1.77-1.25 (m, 6H), 0.72 (d, J=6.0 Hz, 3H). LC/MS (Method B): 269.2 (M+H)+.

後処理

  1. washwas washed with water, NaHCO3
  2. dry with materialOrganics were dried over MgSO4
  3. customevaporated under vacuum

出典と根拠

ORDレコード
ord-ee507c57531140679b462282e08056b7
出典データセット
uspto-grants-2014_06
特許番号
US08741923B2

関連ノート

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