Isoamylamine → HCID 18676169, 화합물

HRID 1635576노트

반응식

HRID 1635576 반응식
[CH2:1]([NH2:6])[CH2:2][CH:3]([CH3:5])[CH3:4].ClC1C=CC=CC=1C[N:11]1[C:15]([CH3:16])=[C:14]([CH3:17])[N:13]=[C:12]1[CH2:18]Cl.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:16][C:15]1[N:11]=[C:12]([CH2:18][NH:6][CH2:1][CH2:2][CH:3]([CH3:5])[CH3:4])[NH:13][C:14]=1[CH3:17]

참가 물질

5

반응물 3

HCID 7894IsoamylamineHCID 11430Potassium CarbonateHCID 12011185HCID 12011185, 화합물

생성물 1

HCID 18676169HCID 18676169, 화합물수율 46%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

실험 절차

To a solution of 7 ml (60 mmol) of isoamylamine in 3 ml of acetonitrile is added slowly a solution of 1-(2′-chlorobenzyl)-4,5-dimethyl-2-chloromethylimidazole in 10 ml of acetonitrile followed by added 1.5 g (10.8 mmol) of potassium carbonate powder. The reaction mixture is stirred overnight at room temperature under nitrogen and excess isoamylamine is evaporated in vacuo. The residue is dissolved in 50 ml of ethyl acetate and 25 ml of water. The ethyl acetate layer is separated, washed with brine, dried over anhydrous sodium sulfate and evaporated in vacuo. The crude product is purified by preparative TLC [silica gel, chloroform-methanol-ammonium hydroxide (90:10:1)] to give 1.39 g (46%) of N-[(4,5-dimethylimidazol-2-yl)methyl]-(3-methylbutyl)amine as a yellow oil. MS m/z (M++1) 320; 1H-NMR 400 MHz(δ, CDCl3): 0.81 (6H, d, J=6.4 Hz), 1.25 (2H, m), 1.51 (1H, m), 1.96 (3H, s), 2.17 (3H, s), 2.56 (2H, m), 3.68 (2H, s), 5.21 (2H, s), 6.39 (1H, d, J=7.6 Hz), 7.13 (1H, m), 7.19 (1H, m), 7.37 (1H, m) ppm.

후처리

  1. customexcess isoamylamine is evaporated in vacuo
  2. dissolutionThe residue is dissolved in 50 ml of ethyl acetate
  3. customThe ethyl acetate layer is separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated in vacuo
  7. customThe crude product is purified by preparative TLC [silica gel, chloroform-methanol-ammonium hydroxide (90:10:1)]

출처 및 근거

ORD 기록
ord-b2fdecc3cf4e4be0ba07bd509a676881
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06509366B2

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