4-Chlorobenzylamine → HCID 16073915, compound

HRID 1068039Notes

Reaction equation

HRID 1068039 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:17]3[C:12](=[CH:13][C:14]([CH2:18][N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)=[CH:15][CH:16]=3)[C:11](=[O:25])[C:10]([C:26]([O:28]CC)=O)=[CH:9]2)[CH2:4][CH2:3]1.[Cl:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH2:37])=[CH:34][CH:33]=1>>[Cl:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36][NH:37][C:26]([C:10]2[C:11](=[O:25])[C:12]3[C:17](=[CH:16][CH:15]=[C:14]([CH2:18][N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH:13]=3)[N:8]([CH:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)[CH:9]=2)=[O:28])=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 21192569HCID 21192569, compound

Product 1

HCID 16073915HCID 16073915, compound

Conditions

Temperature
165 °C

Procedure

A flask containing crude ethyl 1-(1-methyl-4-piperidinyl)-6-(4-morpholinylmethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylate (0.31 g) is treated with 4-chlorobenzylarnine (2.0 mL). The reaction is tightly capped and heated to 165° C. overnight. The reaction is cooled to room temperature, adsorbed onto silica and chromatographed on silica eluting with 2% to 10% methanol saturated with ammonia in dichloromethane and then by recrystallization from ethyl acetate-hexanes to afford 0.11 g of the title compound.

Workup

  1. customThe reaction is tightly capped
  2. temperatureThe reaction is cooled to room temperature
  3. customchromatographed on silica eluting with 2% to 10% methanol saturated with ammonia in dichloromethane
  4. customby recrystallization from ethyl acetate-hexanes

Sources & evidence

ORD record
ord-dc05ad74788b43a2b8c75fb93692dc0c
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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