Hydrogen Bromide → 3-(Methyl(3-phenylpropyl)amino)-5-hydroxychroman

HRID 37655

반응식

HRID 37655 반응식
[NH2:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:12]C)[O:4][CH2:3]1.C([BH3-])#N.[Na+].[C:18]1([CH2:24][CH2:25][CH:26]=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:28]=O.Br.[OH-].[Na+]>CO.C1(C)C=CC=CC=1.C(O)(=O)C>[CH3:28][N:1]([CH2:26][CH2:25][CH2:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:12])[O:4][CH2:3]1

참가 물질

10

반응물 6

HCID 260Hydrogen BromideHCID 712FormaldehydeHCID 7707BenzenepropanalHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydride2회HCID 139289485-Methoxy-3,4-dihydro-2H-1-benzopyran-3-amine

생성물 1

HCID 190281563-(Methyl(3-phenylpropyl)amino)-5-hydroxychroman

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 887Methanol용매HCID 1140Toluene용매

반응 조건

온도
0 °C

실험 절차

3-Amino-5-methoxychroman (Thorberg et al. Acta Pharm. Suec. 24(1987)) (2.0 g, 9.28 mmol) was dissolved in methanol (50 ml) and pH was adjusted to 6.0 with acetic acid. The solution was cooled to 0° C. and sodium cyanoborohydrid (0.87 g, 13.8 mmol) was added together with 3-phenylpropanal (1.22 ml, 9.28 mmol), the cooling was withdrawn and the solution was stirred at ambient temperature for 4 hours. Paraformaldehyde (0.42 g, 14 mmol) and sodium cyanoborohydride (0.87 g, 9.28 mmol) was added and stirring was continued overnight at ambient temperature. The solution was diluted with toluene and washed with water. Drying with sodium sulfate and evaporation to dryness gives an oil. The oil was purified by flash chromatography on silica gel by elution with ethylacete/hexane 1:4. The collected fractions were evaporated to give an oil. The oil was treated with HBr (47% aq.) at 120° C. for 1 hour. The solution was cooled and neutralised with sodium hydroxide and extracted with toluene. The organic phase was dried and evaporated to give the title compound as an oil. 13C-NMR: 22.502 29.09 33.47 38.19 53.66 67.75 102.04 109.20 110.46 125.78 127.05 128.36 142.20 155.29 158.28.

후처리

  1. customthe cooling was withdrawn
  2. stirringstirring
  3. waitwas continued overnight at ambient temperature
  4. washwashed with water
  5. dry with materialDrying with sodium sulfate and evaporation to dryness
  6. customgives an oil
  7. customThe oil was purified by flash chromatography on silica gel by elution with ethylacete/hexane 1:4
  8. customThe collected fractions were evaporated
  9. customto give an oil
  10. temperatureThe solution was cooled
  11. extractionextracted with toluene
  12. customThe organic phase was dried
  13. customevaporated

출처 및 근거

ORD 기록
ord-256a891971184aa7b2d20ad7b29aba8d
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420151

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