Pyridine → 3-(Bromomethyl)-1-methylpiperidine

HRID 1186902

반응식

HRID 1186902 반응식
O[CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([CH3:9])[CH2:4]1.N1C=CC=CC=1.[Br:16]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(#N)C>[Br:16][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][N:5]([CH3:9])[CH2:4]1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 70579Triphenylphosphine dibromideHCID 97998(1-Methyl-3-piperidyl)methanol

생성물 1

HCID 219309923-(Bromomethyl)-1-methylpiperidine수율 105.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
0 °C

실험 절차

3-(Hydroxymethyl)-1-methylpiperidine (2 g, 15.5 mmoles) was dissolved in anhydrous acetonitrile (32 mL) and anhydrous pyridine (2.02 mL, 24.8 mmoles) was added and the solution was cooled to 0° C. Dibromotriphenylphosphorane (8.49 g, 20.2 mmoles) was added at 0° C. and the mixture was allowed to warm up to 25° C. and was stirred for 94 h. The mixture was evaporated to dryness and the residue was chromatographed on a silica gel column (30×5 cm) using gradient elution with dichloromethane, 35% diethyl ether in dichloromethane and 5-10% methanol in dichloromethane as the eluant to give 3-(bromomethyl)-1-methylpiperidine (3.13 g, 100%): FABMS: m/z 192.1 (MH+); δH (CDCl3) 1.52 (1H, m, CH2), 1.99 (2H, m, CH2), 2.43 (1H, m, CH2), 2.75 (2H, m, CH2), 2.82 (1H, m, CH), 2.86/2.88 (3H, s, NCH3), 3.42/3.49 (2H, dd, —CH2Br) and 3.56 ppm (2H, m, CH2); δC (CDCl3) CH3: 44.3; CH2: 22.1, 26.6, 35.4, 54.8, 58.2; CH: 34.6.

후처리

  1. temperatureto warm up to 25° C.
  2. customThe mixture was evaporated to dryness
  3. customthe residue was chromatographed on a silica gel column (30×5 cm)
  4. washelution with dichloromethane, 35% diethyl ether in dichloromethane and 5-10% methanol in dichloromethane as the eluant

출처 및 근거

ORD 기록
ord-8d2266db30614c06aa84d03d6c9b90a6
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673924B2

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