1-Heptanamine → N-[6-(4,5-diphenyl-1-[(trimethylsilyl)ethoxymethyl]-1H-imidazol-2-yl)hexyl]-N-heptylamine

HRID 374068Notes

Reaction equation

HRID 374068 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:12]=1.[CH2:33]([NH2:40])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39].C(=O)(O)[O-].[Na+]>C(#N)C>[C:13]1([C:11]2[N:12]=[C:8]([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:40][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])[N:9]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:10]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 81271-HeptanamineHCID 516892Sodium BicarbonateHCID 10414091HCID 10414091, compound

Product 1

HCID 10256931N-[6-(4,5-diphenyl-1-[(trimethylsilyl)ethoxymethyl]-1H-imidazol-2-yl)hexyl]-N-heptylamineYield 96.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Part B. A solution of 6-bromo-1-(4,5-diphenyl-1-[(trimethylsilyl)ethoxymethyl]-1H-imidazol-2-yl)hexane (1.0 g, 0.00195 mol) and n-heptylamine (0.45 g, 0.00389 mol) in acetonitrile (25 mL) was heated to 60° for 8 hours. The reaction mixture was poured into 10% aqueous sodium bicarbonate and extracted with ethyl acetate (2×50 mL). The combined organic extract was washed with water, brine, dried over magnesium sulfate and concentrated to give N-[6-(4,5-diphenyl-1-[(trimethylsilyl)ethoxymethyl]-1H-imidazol-2-yl)hexyl]-N-heptylamine as a colorless viscous oil (1.04 g, 0.00189 mol). 1H NMR (CDCl3) δ7.52-7.2(m,10H), 5.11(s,2H), 4.7-4.2(bs,1H), 3.3(t,2H), 2.93-2.70(m,6H), 1.95-1.34(m,18H), 0.93(t,3H), 0.86(t,2H), 0.005(s,9H).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. extractionThe combined organic extract
  3. washwas washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c2ccfc958c7649e6be16fb3832bf8372
Source dataset
uspto-grants-1992_11
Patent number
US05166214

Reaction notes

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