Formaldehyde formic acid → 4-methyl-3-((1-methyl-2-(S)-pyrrolidinyl)methoxy)pyridine dihydrochloride

HRID 1416612노트

반응식

HRID 1416612 반응식
[ClH:1].Cl.[CH3:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[O:10][CH2:11][C@@H:12]1[CH2:16][CH2:15][CH2:14][NH:13]1.[CH:17](O)=O.C=O>>[ClH:1].[ClH:1].[CH3:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[O:10][CH2:11][C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH3:17]

참가 물질

3

반응물 2

HCID 18761834Formaldehyde formic acidHCID 213097024-methyl-3-(2-(S)-pyrrolidinylmethoxy)pyridine dihydrochloride

생성물 1

HCID 675852194-methyl-3-((1-methyl-2-(S)-pyrrolidinyl)methoxy)pyridine dihydrochloride

실험 절차

To a 330 mg sample of 4methyl-3-(2-(S)-pyrrolidinylmethoxy)pyridine (from Example 27 above) was added a solution of formic acid/ formaldehyde (1:2,2 mL). The mixture was heated at reflux for 5 hours, and the volatiles were removed by evaporation. The residue was dissolved in 1 mL of 20% NaOH. The solution was extracted with CH2Cl2 (3X), then the organic layer was dried (Na2SO4) and concentrated. The crude product was purified by chromatography over silica gel to afford 295 mg of the title compound. MS (DCI/NH3) m/e: 207 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 8.17 (s, 1H), 8.12 (d, J=5.5 Hz, 1H), 7.06 (d, J=5.5 Hz, 1H), 4.07 (dd, J=3.3, 10.6 Hz, 1H), 3.98 (dd, J=7.4, 10.6 Hz, 1H), 3.15-3.08 (m, 1H), 2.76-2.68 (m, 1H), 2.53 (s, 3H), 2.38-2.25 (m, 1H), 2.26 (s, 3H), 2.12-1.67 (m, 4H).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 5 hours
  3. customthe volatiles were removed by evaporation
  4. dissolutionThe residue was dissolved in 1 mL of 20% NaOH
  5. extractionThe solution was extracted with CH2Cl2 (3X)
  6. dry with materialthe organic layer was dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by chromatography over silica gel

출처 및 근거

ORD 기록
ord-dd788ce24ee74b5fa2908fdbe7b25643
출처 데이터셋
uspto-grants-1999_06
특허 번호
US05914328

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