Hydrochloric Acid → 1-(3-Aminopropyl)-4-cyclohexylpiperidine

HRID 964247ノート

反応式

HRID 964247 の反応式
[CH:1]1([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]#[N:16])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.CCOCC>C1COCC1>[NH2:16][CH2:15][CH2:14][CH2:13][N:10]1[CH2:9][CH2:8][CH:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:12][CH2:11]1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 230041553-(4-Cyclohexylpiperidin-1-yl)propionitrile

生成物 1

HCID 230041241-(3-Aminopropyl)-4-cyclohexylpiperidine収率 88.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred solution of 3-(4-cyclohexylpiperidin-1-yl)propionitrile (5.11 g, 23.3 mmol, 1.0 equiv) in anhydrous THF (15 mL) under argon was added a solution of BH3 in THF (1.0M, 82 mL, 3.5 equiv) at room temperature. The mixture was refluxed for 4.5 hours, then cooled to room temperature and concentrated to a volume of about 30 mL. Aqueous HCl (6N, 55 mL) was added and stirring was continued for 2 hours at 55°-60° C. The mixture was basified to pH 9 by addition of 6N aq. NaOH and extracted with CH2Cl2 (3×100 mL). The combined organic solutions were dried over MgSO4 and concentrated. The residue was dissolved in CH2Cl2 (20 mL) and treated with HCl in ether (1.0M, 58 mL, 2.5 equiv). The solvents were removed, ether (40 mL) was added, the mixture was filtered, and the filter cake was washed with ether (2×20 mL). Water (40 mL) was added to the resulting white solid, the pH was adjusted to 10 with 1M NaOH, and the aqueous phase was extracted with CH2 Cl2 (3×80 mL). The combined organic solutions were dried over MgSO4 and concentrated to give 4.63 g (88%) of colorless oil, which was characterized spectroscopically.

後処理

  1. temperatureThe mixture was refluxed for 4.5 hours
  2. concentrationconcentrated to a volume of about 30 mL
  3. additionAqueous HCl (6N, 55 mL) was added
  4. additionThe mixture was basified to pH 9 by addition of 6N aq. NaOH
  5. extractionextracted with CH2Cl2 (3×100 mL)
  6. dry with materialThe combined organic solutions were dried over MgSO4
  7. concentrationconcentrated
  8. dissolutionThe residue was dissolved in CH2Cl2 (20 mL)
  9. customThe solvents were removed
  10. additionether (40 mL) was added
  11. filtrationthe mixture was filtered
  12. washthe filter cake was washed with ether (2×20 mL)
  13. additionWater (40 mL) was added to the resulting white solid
  14. extractionthe aqueous phase was extracted with CH2 Cl2 (3×80 mL)
  15. dry with materialThe combined organic solutions were dried over MgSO4
  16. concentrationconcentrated

出典と根拠

ORDレコード
ord-e0894ef7ad1f4f36b6658dabc5bff4d3
出典データセット
uspto-grants-1998_06
特許番号
US05767131

反応ノート

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