4-Chlorobenzylamine → HCID 16073914, compound

HRID 1068035Notes

Reaction equation

HRID 1068035 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][O: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[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)[CH:9]=3)[N:14]([CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[CH:13]=2)=[O:25])=[CH:33][CH:32]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 21192606HCID 21192606, compound

Product 1

HCID 16073914HCID 16073914, compound

Conditions

Temperature
190 °C

Procedure

A flask containing ethyl 6-(4-morpholinylmethyl)-4-oxo-1-tetrahydro-2H-pyran-4-yl-1,4-dihydro-3-quinolinecarboxylate (0.21 g) is treated with 4-chlorobenzylamine (2.0 mL). The reaction is tightly capped and heated to 190° C. for 1 hour. The reaction is cooled to room temperature, adsorbed onto silica and chromatographed on silica eluting with 2% to 6% methanol in dichloromethane and then by recrystallization from ethyl acetate to afford 0.14 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 6% methanol in dichloromethane
  4. customby recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-2a995c45f72a4c3fa48f1aa7d42b4721
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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