Hydrochloric Acid → 2-[4-(1-Aminoethyl)phenyl]-2-ethylbutanenitrile

HRID 419978노트

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HRID 419978 반응식
[C:1]([C:3]([C:8]1[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=1)([CH2:6][CH3:7])[CH2:4][CH3:5])#[N:2].[Li]C.[BH4-].[Na+].Cl.[OH-].[Na+].[CH3:23]C#N>CO.O.C1COCC1>[NH2:13][CH:12]([C:11]1[CH:10]=[CH:9][C:8]([C:3]([CH2:4][CH3:5])([CH2:6][CH3:7])[C:1]#[N:2])=[CH:15][CH:14]=1)[CH3:23]

참가 물질

10

반응물 6

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 582984684-(1-Cyano-1-ethylpropyl)benzonitrileHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 582984502-[4-(1-Aminoethyl)phenyl]-2-ethylbutanenitrile

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

4-(1-Cyano-1-ethylpropyl)benzonitrile (936 mg, 5.51 mmol) is added to THF (20.0 mL), and the resulting solution is cooled to −78° C. MeLi (3.44 mL, 5.51 mmol) is added, and the solution is stirred for 20 minutes. NaBH4 (208 mg, 5.51 mmol) is mixed in MeOH (20.0 mL) and added to the first solution. The resulting solution is warmed to room temperature and stirred for 1 hour. 1N HCl (50.0 mL) is added followed by 1N NaOH (60.0 mL). The aqueous phase is extracted with EtOAc (4 times 50.0 mL) and the combined organic phases are dried with MgSO4, filtered and concentrated on the rotovaporator. The product is purified by HPLC: Gilson prep pumps, Flow rate: 30 ml/min, Column: Gemini (5u) 21.2×50 mm, Mobile phase: A=water (10 mM NH4CO3) B=MeCN, (528 mg, 2.44 mmol, 44%). 1H NMR (400 MHz, DMSO-D6) δ ppm 0.77 (t, J=7.32 Hz, 6H) 1.22 (d, J=6.45 Hz, 3H) 1.82-2.07 (m, 4H) 3.97 (q, J=6.64 Hz, 1H) 7.32 (d, J=8.40 Hz, 2H) 7.40 (d, J=8.20 Hz, 2H).

후처리

  1. additionadded to the first solution
  2. temperatureThe resulting solution is warmed to room temperature
  3. stirringstirred for 1 hour
  4. extractionThe aqueous phase is extracted with EtOAc (4 times 50.0 mL)
  5. dry with materialthe combined organic phases are dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated on the rotovaporator
  8. customThe product is purified by HPLC

출처 및 근거

ORD 기록
ord-5c7a39cae4af4ec4b8717e249ee6f268
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093402B2

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