Triethylamine → 1-cyclohexyl-N-[(1S)-1-(furan-2-yl)ethyl]piperidin-4-amine

HRID 1618114노트

반응식

HRID 1618114 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C@@H:6]([NH2:8])[CH3:7].[CH:9]1([N:15]2[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C(N(CC)CC)C.C([BH3-])#N.[Na+]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl.CO>[CH:9]1([N:15]2[CH2:20][CH2:19][CH:18]([NH:8][C@H:6]([C:2]3[O:1][CH:5]=[CH:4][CH:3]=3)[CH3:7])[CH2:17][CH2:16]2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 7047669(1S)-1-(furan-2-yl)ethan-1-amineHCID 122527641-Cyclohexylpiperidin-4-one

생성물 1

HCID 671921261-cyclohexyl-N-[(1S)-1-(furan-2-yl)ethyl]piperidin-4-amine수율 52.1%

시약·촉매·용매 3

HCID 24193Titanium Tetrachloride촉매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

(1S)-1-(Furan-2-yl)ethanamine (0.55 gr, 5 mmol) and 1-cyclohexylpiperidin-4-one (0.91 gr, 5 mmol) were dissolved in dry dichloromethane (20 mL) in the presence of triethylamine (2 mL, 15 mmol) and titanium(IV) chloride (1M in dichloromethane, 2.5 mmol, 2.5 mL). Reaction mixture was stirred under nitrogen atmosphere for 16 hours. After dilution with methanol (10 mL), sodium cyanoborohydride was added (0.95 gr, 25 mmol) and the resulting reaction mixture was stirred for 4 hours. After dilution with ethyl acetate, the organic phase was washed with 15% ammonium hydroxide and evaporated to dryness. Title compound (0.72 gr, Y=52%) was isolated by column chromatography (dichloromethane/methanol/7N ammonia in methanol 96:2:2)

후처리

  1. customReaction mixture
  2. customthe resulting reaction mixture
  3. stirringwas stirred for 4 hours
  4. washAfter dilution with ethyl acetate, the organic phase was washed with 15% ammonium hydroxide
  5. customevaporated to dryness

출처 및 근거

ORD 기록
ord-687ca5b695e643df81bb412f7b85e413
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765972B2

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