Benzoyl chloride → HCID 68776815, compound

HRID 408662Notes

Reaction equation

HRID 408662 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:23])[CH:8]=2)[N:3]=1.[C:24]([Cl:32])(=[O:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(NC(C)C)(C)C>ClCCl.[OH-].[Na+]>[ClH:32].[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:16][CH2:15][CH:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH:23][C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:8]=2)[N:3]=1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 7912DiisopropylamineHCID 68725336HCID 68725336, compound

Product 1

HCID 68776815HCID 68776815, compoundYield 29.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

2-Methyl-6-amino-4-(3-phenylpyrrolidin-1-yl)quinoline (0.07 g; see Example 45 below), benzoyl chloride (0.035 g) and diisopropylamine (0.065 g) was stirred in dichloromethane (3 mL). The reaction mixture was diluted with 1 N sodium hydroxide and extracted with ethyl acetate, washed with water, dried (MgSO4), filtered and evaporated to give a brown oil. The residue was purified by chromatography on silica eluting with a mixture of dichloromethane, and methanol. The desired fractions were concentrated, after which hydrochloric acid was added and the sample evaporated to dryness. Trituration from ether gave the title compound as a white solid (0.03 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto give a brown oil
  7. customThe residue was purified by chromatography on silica eluting with a mixture of dichloromethane, and methanol
  8. concentrationThe desired fractions were concentrated
  9. additionafter which hydrochloric acid was added
  10. customthe sample evaporated to dryness

Sources & evidence

ORD record
ord-a3a791ec876b4e5ba2eb0d467dafb17d
Source dataset
uspto-grants-2014_06
Patent number
US08759348B2

Reaction notes

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