Potassium Carbonate → cis-1-(4-Bromobenzyl)-3,5-dimethylpiperidine

HRID 1505923ノート

反応式

HRID 1505923 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[CH3:10][C@H:11]1[CH2:16][C@H:15]([CH3:17])[CH2:14][NH:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:13]2[CH2:14][C@H:15]([CH3:17])[CH2:16][C@H:11]([CH3:10])[CH2:12]2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 7058087(3S,5S)-3,5-dimethylpiperidine

生成物 1

HCID 58266703cis-1-(4-Bromobenzyl)-3,5-dimethylpiperidine収率 35.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A suspension of 4-bromobenzyl bromide (4.0 g, 16.0 mmol), cis, trans-(3,5-dimethylpiperidine) (1.81 g, 16.0 mmol) and potassium carbonate (2.65 g, 19.2 mmol) in THF (160 mL) was heated under reflux for 24 h. The reaction mixture was allowed to cool to ambient temperature, the solid removed by filtration and the filtrate evaporated in vacuo. The resultant residue was loaded onto a 50 g SCX-2 cartridge which was washed with methanol then eluted with 2N ammonia in methanol. Concentration of the combined basic fractions in vacuo followed by flash chromatography of the resultant residue (silica, 330 g column, ISCO, 0-25% ethyl acetate in pentane) afforded cis-1-(4-bromobenzyl)-3,5-dimethylpiperidine (1.60 g, 35%) as a colourless oil. 1H NMR (CDCl3, 300 MHz): 7.47-7.39 (m, 2H); 7.20 (d, J=8.0 Hz, 2H); 3.42 (s, 2H); 2.82-2.71 (m, 2H); 1.76-1.61 (m, 4H); 1.51-1.37 (m, 2H); 0.82 (d, J=6.4 Hz, 6H).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 24 h
  3. customthe solid removed by filtration
  4. customthe filtrate evaporated in vacuo
  5. washwas washed with methanol
  6. washthen eluted with 2N ammonia in methanol

出典と根拠

ORDレコード
ord-e57691bc1b5e45b093ecd71e34c04123
出典データセット
uspto-grants-2015_12
特許番号
US09216980B2

反応ノート

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