Methanol → Piperidine, 1-(5-methoxy-2-nitrophenyl)-

HRID 32887

反応式

HRID 32887 の反応式
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]=1.[CH3:17][O-:18].[Na+].CO>CN(C=O)C.CCOC(C)=O>[CH3:17][O:18][C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]=1

参加物

6

反応物 3

HCID 887MethanolHCID 30960791-(5-Chloro-2-nitrophenyl)piperidineHCID 10942334Sodium Methoxide

生成物 1

HCID 69310428Piperidine, 1-(5-methoxy-2-nitrophenyl)-収率 41%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To 1-(5-chloro-2-nitro-phenyl)-piperidine (197 mg, 0.810 mmol) in 1.5 mL of DMF was added 4 mL of 0.5 M NaOMe in MeOH (2.5 eq). The resultant solution was heated at 60° C. overnight, then at 90° C. for 24 h. The reaction was diluted with EtOAc (50 mL) and washed with water (50 mL), dried (Na2SO4) and concentrated in vacuo. Purification by preparative TLC (20% EtOAc-hexane) gave 80 mg (41%) of the title compound, along with 80 mg (40%) of recovered starting material. 1H-NMR (CDCl3; 400 MHz): δ 7.95 (d, 1H, J=9.1 Hz), 6.51 (d, 1H, J=2.6 Hz), 6.46 (dd, 1H, J=2.6, 9.1 Hz), 3.87 (s, 3H), 3.01-3.04 (m, 4H), 1.72-1.78 (m, 4H), 1.60-1.64 (m, 2H).

後処理

  1. washwashed with water (50 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customPurification by preparative TLC (20% EtOAc-hexane)

出典と根拠

ORDレコード
ord-4415a01d13f14a71a7183f8e8589ba6a
出典データセット
uspto-grants-2008_09
特許番号
US07427683B2

関連ノート

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