2-Chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline → HCID 178419790, compound

HRID 1082046Notes

Reaction equation

HRID 1082046 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.[NH:14]1[CH:18]=[C:17]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[N:16]=[CH:15]1>C(O)CC(C)C>[NH:14]1[CH:18]=[C:17]([CH:19]2[CH2:24][CH2:23][N:22]([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)[CH2:21][CH2:20]2)[N:16]=[CH:15]1

Participants

4

Reactant 2

HCID 152871052-Chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolineHCID 1784208734-(1H-imidazol-4-yl)piperidine

Product 1

HCID 178419790HCID 178419790, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

1 g (0.0052 mol) of 2-chloro-5,6-dihydro-4H-imidazo[4,5,1-ij]quinoline, 1.57 g (0.0104 mol) of 4-(1H-imidazol-4-yl)piperidine and 5 ml of isoamyl alcohol are heated at 120° C. for 1 day. The alcohol is then evaporated to dryness, the residue is taken up in a water/ether (50/50) mixture and the product sucked dry. The product is purified by chromatography on a column of silica gel, the eluent being a dichloromethane/methanol/aqueous ammonia (95/5/0.5) mixture, is then triturated in ether and dried under vacuum at 60° C. 1 g of product is obtained.

Workup

  1. customThe alcohol is then evaporated to dryness
  2. customthe product sucked dry
  3. customThe product is purified by chromatography on a column of silica gel
  4. customis then triturated in ether
  5. customdried under vacuum at 60° C

Sources & evidence

ORD record
ord-641dcc8a4a014a4eb165ee6f1660dab6
Source dataset
uspto-grants-1996_12
Patent number
US05589476

Reaction notes

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