Formic Acid → 3-(1-Methylpyrrolidin-2-yl)pyridine

HRID 384843

반응식

HRID 384843 반응식
[CH:1]1[CH:6]=[N:5][CH:4]=[C:3]([CH:7]2[NH:11][CH2:10][CH2:9][CH2:8]2)[CH:2]=1.C=O.[CH:14](O)=O.[OH-].[Na+]>O>[CH3:14][N:11]1[CH:7]([C:3]2[CH:2]=[CH:1][CH:6]=[N:5][CH:4]=2)[CH2:8][CH2:9][CH2:10]1

참가 물질

6

반응물 4

HCID 284Formic AcidHCID 4123-(Pyrrolidin-2-yl)pyridineHCID 712FormaldehydeHCID 14798Sodium Hydroxide

생성물 1

HCID 9423-(1-Methylpyrrolidin-2-yl)pyridine수율 81.3%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
85 °C

실험 절차

To a solution of nornicotine (50 g 0.338 mol) in 100 ml water a mixture of 37% formaldehyde (49.7 g, 1.656 mol) and 85% formic acid (37.26 g 0.81 moles) was added and stirred at 85° C. for 20 hrs. The reaction was cooled and pH adjusted to >13 using NaOH, extracted with dichloromethane (100 ml×3) dried over Na2SO4 and solvent removed completely to get crude oil (52.5 g, 94.33% purity by GC). It was further purified by high vacuum distillation at 0.1 mm Hg to obtain colorless (R,S)-nicotine (44.54 g, 81.3% yield, 99.1% purity by GC). 1H NMR (CDCl3): δ 1.72-2.0 (3H, m), 2.1 (3H, s), 2.25 (1H, m), 2.3 (1H, m), 3.08 (1H, m), 3.23 (1h, t), 7.25 (1H, m), 7.69 (1H, dt), and 8.5 (2H, m). 13C-NMR (CDCl3): 149.71, 148.76, 139, 134.97, 123.7, 68.9, 57.1, 40.5, 35.5, and 22.83. IR: 3233, 1642, and 1402 Cm−1.

후처리

  1. additionwas added
  2. temperatureThe reaction was cooled
  3. extractionextracted with dichloromethane (100 ml×3)
  4. dry with materialdried over Na2SO4 and solvent
  5. customremoved completely
  6. customto get crude oil (52.5 g, 94.33% purity by GC)
  7. distillationIt was further purified by high vacuum distillation at 0.1 mm Hg

출처 및 근거

ORD 기록
ord-6d87d8eeef23493ea584d57aa0c9e664
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367837B2

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