Triethylamine → 2-[4-(4-Bromophenoxy)-3-phenyl-1-piperidinyl]-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline

HRID 1440708Notes

Reaction equation

HRID 1440708 reaction equation
Cl[C:2]1[N:12]2[C:13]3[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=1.[Br:14][C:15]1[CH:33]=[CH:32][C:18]([O:19][CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH:21]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:17][CH:16]=1.C(N(CC)CC)C>CN(C)C=O>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([O:19][CH:20]2[CH2:25][CH2:24][N:23]([C:2]3[N:12]4[C:13]5[C:8]([CH2:9][CH2:10][CH2:11]4)=[CH:7][CH:6]=[CH:5][C:4]=5[N:3]=3)[CH2:22][CH:21]2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 130392894-(4-Bromophenoxy)-3-phenylpiperidineHCID 152871052-Chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline

Product 1

HCID 189819362-[4-(4-Bromophenoxy)-3-phenyl-1-piperidinyl]-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolineYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline (3.00 g), 4-(4-bromophenoxy)-3-phenylpiperidine (5.20 g), triethylamine (1.62 g) and dimethylformamide (50 ml) was stirred at 115° C., under nitrogen, overnight. The solution was poured onto ice water (600 ml) and the precipitate was collected. The precipitate was dissolved in dichloromethane and the solution was washed with brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated. The residue was triturated with ethyl acetate and then recrystallized from chloroform-ether to give 4.25 g (56%) of product, mp 188°-189° C.

Workup

  1. additionThe solution was poured onto ice water (600 ml)
  2. customthe precipitate was collected
  3. dissolutionThe precipitate was dissolved in dichloromethane
  4. washthe solution was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated
  8. customThe residue was triturated with ethyl acetate
  9. customrecrystallized from chloroform-ether

Sources & evidence

ORD record
ord-2d123a315a074d19b7c5fe23cd715689
Source dataset
uspto-grants-1996_03
Patent number
US05500423

Reaction notes

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