Methanol → N-Allyl-N,N-di-n-octylamine

HRID 1019357

반응식

HRID 1019357 반응식
[CH2:1]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:18](Br)[CH:19]=[CH2:20].CCN(C(C)C)C(C)C.CO>CN(C=O)C.C(Cl)Cl>[CH2:20]([N:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH:19]=[CH2:18]

참가 물질

7

반응물 4

HCID 887MethanolHCID 3094DioctylamineHCID 7841Allyl bromideHCID 81531Diisopropylethylamine

생성물 1

HCID 4562804N-Allyl-N,N-di-n-octylamine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

Vinylsulfomethylpolystyrene resin 3 (0.42 mmol g−1 (est), 160 mg) in DMF (2 cm3) was treated with dioctylamine (1.7 mmol, 515 mm3) at 20° C. for 24 h. The resin was washed with DMF (10×5 cm3) and DCM (10 cm3), resuspended in DMF (2 cm3) and treated with allyl bromide (4.25 mmol, 365 mm3) at 20° C. for 24 h. The solvent and the reagent was then removed by filtration and the resin washed with DCM (2×20 cm3). The elimination was performed in DCM (4 cm3) with DIEA (1.72 mmol, 300 mm3) overnight. The filtrate of this last reaction step was combined with the DCM and MeOH, washed (25 cm3) from the resin and evaporated. It gave 14 contaminated with DIEA in 38 mg yield. The amine was transferred in a little DCM (<5 cm3) to a K2CO3 covered dry silica column (5 g). Impurities were washed away with hexane and the amine eluted with ethyl acetate. After the removal of the solvent 14 was obtained as a colorless oil.

후처리

  1. washThe resin was washed with DMF (10×5 cm3) and DCM (10 cm3)
  2. customThe solvent and the reagent was then removed by filtration
  3. washthe resin washed with DCM (2×20 cm3)
  4. customThe filtrate of this last reaction step
  5. washwashed (25 cm3) from the resin
  6. customevaporated

출처 및 근거

ORD 기록
ord-16cd478fae0741f69f5e2b4551b2edea
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06486354B1

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