4-Chlorobenzylamine → HCID 10159541, compound

HRID 411227Notes

Reaction equation

HRID 411227 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[Cl:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=1.C([O:16][C:17]([C:19]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][N:24]=[C:25]([CH2:30][N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[CH:26]=2)[N:21]([CH3:37])[CH:20]=1)=O)C>C1(C)C=CC=CC=1.C(Cl)Cl>[Cl:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH:11][C:17]([C:19]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][N:24]=[C:25]([CH2:30][N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)[CH:26]=3)[N:21]([CH3:37])[CH:20]=2)=[O:16])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 660364-ChlorobenzylamineHCID 6451240Aluminum(III) ChlorideHCID 22397176HCID 22397176, compound

Product 1

HCID 10159541HCID 10159541, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

At 0° C., a solution of 2.0M AlCl3 in toluene (0.14 mL) is added to a solution of 4-chlorobenzylamine (0.044 mL) in CH2Cl2 (5 mL). The compound from ethyl-1-methyl-6-(4-morpholinylmethyl)-4-oxo-1,4-dihydro[1,7]naphthyridine-3-carboxylate (Preparation 46, 0.058 g) is added and the mixture allowed to stir at room temperature for 3 hours at which time the mixture is partitioned between CH2Cl2 (30 mL) and water (30 mL). The organics are dried with Na2SO4, filtered and the solvent evaporated. The remaining solid is chromatographed with MeOH/CH2Cl2 (1-4%) to obtain 0.049 g (67%) of the title compound as an off-white solid. Physical characteristics: MS (ESI+) m/z 427 (M+H).

Workup

  1. customis partitioned between CH2Cl2 (30 mL) and water (30 mL)
  2. dry with materialThe organics are dried with Na2SO4
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. customThe remaining solid is chromatographed with MeOH/CH2Cl2 (1-4%)

Sources & evidence

ORD record
ord-6716d4f891884d31ab46fc8984b2b9ce
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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