Tert-Butylamine → HCID 89422940, 화합물

HRID 1481680노트

반응식

HRID 1481680 반응식
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12](=O)[CH2:13][CH2:14][CH3:15])=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH2:3]1.[CH3:17][C:18]([NH2:21])([CH3:20])[CH3:19]>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:17][C:18]([N:21]=[C:12]([C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[N:2]([CH3:1])[CH2:3][CH2:4][CH2:5]2)[CH2:13][CH2:14][CH3:15])([CH3:20])[CH3:19]

참가 물질

5

반응물 2

HCID 6385Tert-ButylamineHCID 39104401HCID 39104401, 화합물

생성물 1

HCID 89422940HCID 89422940, 화합물

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)butan-1-one (2.94 g, 13.5 mmol) in CH2Cl2 (14 mL) was added 2-methylpropan-2-amine (5.7 mL, 54.2 mmol, 4.0 eq). The mixture was cooled to 0° C. before TiCl4 (1.0M in CH2Cl2, 8.8 mL, 8.8 mmol, 0.65 eq) was added via syringe pump over 30 min. The reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was quenched with saturated aqueous NaHCO3 (15 mL) then extracted by CH2Cl2 (5×25 mL). The combined organic layers were dried over Na2SO4 then concentrated to give a crude product which was carried over to next step without further purification. LC-MS 273.1 [M+H]+, RT 0.65 min. (1 min Method).

후처리

  1. additionwas added via syringe pump over 30 min
  2. customThe reaction mixture was quenched with saturated aqueous NaHCO3 (15 mL)
  3. extractionthen extracted by CH2Cl2 (5×25 mL)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationthen concentrated

출처 및 근거

ORD 기록
ord-9b2bb029956d44299353139e2611a6a5
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409905B2

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