Hydrochloric Acid → (+)-4-(4-Fluorophenyl)-1,2,3,6-tetrahydro-1-(phenylmethyl)-3-pyridinemethanol

HRID 1858714노트

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HRID 1858714 반응식
[CH2:1]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH2:22]=[O:23].[OH-].[Na+]>O>[CH2:1]([N:8]1[CH2:9][CH:10]=[C:11]([C:14]2[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=2)[CH:12]([CH2:22][OH:23])[CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 100615101-Benzyl-4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine

생성물 1

HCID 9912522(+)-4-(4-Fluorophenyl)-1,2,3,6-tetrahydro-1-(phenylmethyl)-3-pyridinemethanol수율 78.3%

시약·촉매·용매 1

HCID 962Water용매

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온도
100 °C

실험 절차

4.5 g (16.8 mmol) of 1-benzyl-4-(4-fluoro-phenyl)-1,2,3,6-tetrahydro-pyridine were suspended in 55 ml of water, then partially dissolved by the addition of 70 ml of concentrated hydrochloric acid, 1.36 g (45.3 mmol) of paraformaldehyde were added and the mixture was stirred at 100° C. for 5 hours. After cooling to room temperature the mixture was adjusted to pH 5-6 with sodium hydroxide solution and the product was extracted twice with 100 ml of ethyl acetate. The organic phases were washed once with 100 ml of water, dried over magnesium sulphate, filtered and concentrated in a water-jet vacuum. The thus-obtained crude product was chromatographed on silica gel with hexane and ethyl acetate as the eluent (sic). There were obtained 3.91 g (78% of theory) of (RS)-[1-benzyl-4-(4-fluoro-phenyl)-1,2,3,6-tetrahydro-pyridin-3-yl]-methanol; MS: 297 (M)+.

후처리

  1. additionwere added
  2. temperatureAfter cooling to room temperature the mixture
  3. extractionthe product was extracted twice with 100 ml of ethyl acetate
  4. washThe organic phases were washed once with 100 ml of water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in a water-jet vacuum
  8. customThe thus-obtained crude product
  9. customwas chromatographed on silica gel with hexane and ethyl acetate as the eluent (sic)

출처 및 근거

ORD 기록
ord-07ab4198d4664c73918535376e1146b3
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06150526

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