4-Chlorobenzylamine → HCID 16073916, compound

HRID 1068041Notes

Reaction equation

HRID 1068041 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:13]=[C:12]([C:24](OCC)=[O:25])[C:11]3=[O:29])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH2:36])=[CH:33][CH:32]=1>>[Cl:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][NH:36][C:24]([C:12]2[C:11](=[O:29])[C:10]3[C:15](=[CH:16][CH:17]=[C:8]([CH2:7][N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)[CH:9]=3)[N:14]([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH:13]=2)=[O:25])=[CH:33][CH:32]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 21192537HCID 21192537, compound

Product 1

HCID 16073916HCID 16073916, compound

Conditions

Temperature
180 °C

Procedure

A flask containing crude ethyl 6-(4-morpholinylmethyl)-4-oxo-1-(4-piperidinyl)-1,4-dihydro-3-quinolinecarboxylate (0.14 g) is treated with 4-chlorobenzylamine (1.0 mL). The reaction is tightly capped and heated to 180° C. for 2 hours. The reaction is cooled to room temperature and flash column chromatographed on silica eluting with 2% to 10% methanol saturated with ammonia in dichloromethane and then by recrystallization from acetonitrile to afford 0.10 g of the title compound as a white solid.

Workup

  1. customThe reaction is tightly capped
  2. temperatureThe reaction is cooled to room temperature
  3. customflash column chromatographed on silica eluting with 2% to 10% methanol saturated with ammonia in dichloromethane
  4. customby recrystallization from acetonitrile

Sources & evidence

ORD record
ord-fde7864b822d454a8ade3914a1b4b28e
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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