4-[3-(Methylsulfanyl)phenyl]-1-propylpiperidin-4-ol → 4-[3-(Methylsulfanyl)phenyl]-1-propyl-1,2,3,6-tetrahydro-pyridine

HRID 2280367ノート

反応式

HRID 2280367 の反応式
[CH3:1][S:2][C:3]1[CH:4]=[C:5]([C:9]2(O)[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH3:17])[CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1>FC(F)(F)C(O)=O>[CH3:1][S:2][C:3]1[CH:4]=[C:5]([C:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH3:17])[CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

参加物

3

反応物 1

HCID 299817804-[3-(Methylsulfanyl)phenyl]-1-propylpiperidin-4-ol

生成物 1

HCID 166553434-[3-(Methylsulfanyl)phenyl]-1-propyl-1,2,3,6-tetrahydro-pyridine

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

実験手順

4-(3-Methylsulfanyl-phenyl)-1-propyl-piperidin-4-ol (1) (100 mg, 0.38 mmol) was dissolved in 2 mL of trifluoroacetic acid (TFA) in a 50 mL flask while stirring in a nitrogen atmosphere. The reaction mixture was heated to reflux on an isomantle. After 15 minutes the reaction mixture was cooled to room temperature. The TFA was removed by distillation under reduced pressure. The remaining brown oil was dissolved in diethyl ether, washed 3 times with water and once with brine. The aqueous layers and brine layer were collected, basified with Na2CO3 and extracted with diethyl ether twice. The organic layers were collected, dried on MgSO4, filtered and the solvent was evaporated under reduced pressure using a rotavapor. Yield: 103 mg (111%). GCMS (EI): m/z 247 (M+), 218 (M−29); GC (100-320° C., 15° C./min): 7.6 min.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux on an isomantle
  3. customThe TFA was removed by distillation under reduced pressure
  4. dissolutionThe remaining brown oil was dissolved in diethyl ether
  5. washwashed 3 times with water
  6. customThe aqueous layers and brine layer were collected
  7. extractionextracted with diethyl ether twice
  8. customThe organic layers were collected
  9. customdried on MgSO4
  10. filtrationfiltered
  11. customthe solvent was evaporated under reduced pressure
  12. customGC (100-320° C., 15° C./min)
  13. custom7.6 min.

出典と根拠

ORDレコード
ord-18dd3df15804462e86125706e3c70c57
出典データセット
uspto-grants-2015_09
特許番号
US09139525B2

反応ノート

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