Benzoyl chloride → HCID 18349767, compound

HRID 378604Notes

Reaction equation

HRID 378604 reaction equation
C(N(CC)CC)C.Cl.Cl.Cl.[NH2:11][CH2:12][CH2:13][C:14]1[N:15]=[CH:16][N:17]([CH2:19][CH2:20][CH2:21][NH:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)([CH3:25])[CH3:24])[CH:18]=1.[C:33](Cl)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>ClCCl>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([C:23]([NH:22][CH2:21][CH2:20][CH2:19][N:17]2[CH:18]=[C:14]([CH2:13][CH2:12][NH:11][C:33](=[O:40])[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[N:15]=[CH:16]2)([CH3:25])[CH3:24])=[CH:27][CH:28]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 18349657HCID 18349657, compound

Product 1

HCID 18349767HCID 18349767, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Triethylamine (0.46 g) was added to a stirred suspension of 3-[4-(2-aminoethyl)imidazol-1-yl]-N-[1-(4-chlorophenyl)-1-methylethyl]propylamine trihydrochloride, (0.65 g) in dichloromethane (25 ml) and the resulting solution cooled to 0° C. A solution of benzoyl chloride (0.21 g) in dichloromethane (10 ml) was added over 20 minutes at 0-5° C. with stirring. The mixture was stirred at ambient temperature for 2.5 hours. The solution was washed with sodium bicarbonate solution, then water, then dried, filtered and evaporated to give N-[2-(1-{3-[1-(4-chlorophenyl)-1-methylethylamino]propyl}imidazol-4-yl)ethyl]benzamide as an oil.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 2.5 hours
  2. washThe solution was washed with sodium bicarbonate solution
  3. dry with materialwater, then dried
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-051e0a54f1c542e69e6e46880f30f75d
Source dataset
uspto-grants-2000_02
Patent number
US06031109

Reaction notes

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