Isoamylamine → HCID 18676169, compound

HRID 1635576Notes

Reaction equation

HRID 1635576 reaction equation
[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]

Participants

5

Reactant 3

HCID 7894IsoamylamineHCID 11430Potassium CarbonateHCID 12011185HCID 12011185, compound

Product 1

HCID 18676169HCID 18676169, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

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.

Workup

  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)]

Sources & evidence

ORD record
ord-b2fdecc3cf4e4be0ba07bd509a676881
Source dataset
uspto-grants-2003_01
Patent number
US06509366B2

Reaction notes

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