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

HRID 1505923노트

반응식

HRID 1505923 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-e57691bc1b5e45b093ecd71e34c04123
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216980B2

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