4-Chlorobenzylamine → Jjy8ryh7J4

HRID 1068047Notes

Reaction equation

HRID 1068047 reaction equation
[N:1]1([N:7]2[C:16]3[C:11](=[CH:12][C:13]([CH2:17][N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:14][CH:15]=3)[C:10](=[O:24])[C:9]([C:25](OCC)=[O:26])=[CH:8]2)[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:25]([C:9]2[C:10](=[O:24])[C:11]3[C:16](=[CH:15][CH:14]=[C:13]([CH2:17][N:18]4[CH2:19][CH2:20][O:21][CH2:22][CH2:23]4)[CH:12]=3)[N:7]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[CH:8]=2)=[O:26])=[CH:33][CH:32]=1

Participants

3

Reactant 2

HCID 660364-ChlorobenzylamineHCID 21192510Ethyl 1-(4-morpholinyl)-6-(4-morpholinylmethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylate

Product 1

HCID 490487Jjy8ryh7J4Yield 79%

Conditions

Temperature
190 °C

Procedure

Ethyl 1-(4-morpholinyl)-6-(4-morpholinylmethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylate (5.0 g) from Preparation No. 56 and 4-chlorobenzylamine (7.6 mL) are combined and heated to 190° C. for 7 hours. After cooling to room temperature, the mixture solidifies. The solid is triturated with a 10:1 mixture of EtOAc/MTBE (30 mL) and filtered on a frit. The crude solid is triturated again, this time with a hot mixture of 10:1 EtOAc/MTBE (110 mL). The suspension is cooled to room temperature and filtered on a frit to afford 4.9 g (79%) of the title compound as a white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe solid is triturated with a 10:1 mixture of EtOAc/MTBE (30 mL)
  3. filtrationfiltered on a frit
  4. customThe crude solid is triturated again
  5. additionthis time with a hot mixture of 10:1 EtOAc/MTBE (110 mL)
  6. temperatureThe suspension is cooled to room temperature
  7. filtrationfiltered on a frit

Sources & evidence

ORD record
ord-1debd4cf9fdd49f9858a99d04b8a0dbe
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

Loading…