Benzoyl chloride → HCID 12968612, compound

HRID 651063Notes

Reaction equation

HRID 651063 reaction equation
[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]=1[O:29][CH2:30][CH2:31][NH2:32])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].[C:33](Cl)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl>[CH2:1]([C@H:3]([NH:10][C:11]([C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=[C:15]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:14]=1[O:29][CH2:30][CH2:31][NH:32][C:33](=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 10764865(S)-N-(alpha-ethylbenzyl)-3-(2-aminoethoxy)-2-phenylquinoline-4-carboxamide

Product 1

HCID 12968612HCID 12968612, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

0.95 g (2.2 mmol) of (S)-N-(α-ethylbenzyl)-3-(2-aminoethoxy)-2-phenylquinoline-4-carboxamide (compound of Description 4) were dissolved, under nitrogen atmosphere and magnetical stirring, in 12 ml of dry CH2Cl2; 0.37 ml (2.6 mmol) of TEA were added, the solution cooled to 0° C. and 0.3 ml (2.6 mmol) of benzoyl chloride, dissolved in in 3 ml dry CH2Cl2 were added dropwise. The reaction was left 30 minutes at 0° C., then allowed to reach room temperature and left overnight. The mixture was evaporated in-vacuo to dryness, the residue was dissolved in CH2Cl2, and washed with H2O, 20% citric acid, sat. sol. NaHCO3, sat. sol. NaCl; the organic layer was dried over Na2SO4 and evaporated in-vacuo to dryness. The residue was triturated with hot i-Pr2O/i-PrOH to yield 0.8 g of the title compound as a white solid.

Workup

  1. additionwere added dropwise
  2. customto reach room temperature
  3. waitleft overnight
  4. customThe mixture was evaporated in-vacuo to dryness
  5. dissolutionthe residue was dissolved in CH2Cl2
  6. washwashed with H2O, 20% citric acid, sat. sol. NaHCO3, sat. sol. NaCl
  7. dry with materialthe organic layer was dried over Na2SO4
  8. customevaporated in-vacuo to dryness
  9. customThe residue was triturated with hot i-Pr2O/i-PrOH

Sources & evidence

ORD record
ord-e4434bf5e0c6413da3b5784a1f655fad
Source dataset
uspto-grants-2001_08
Patent number
US06277862B1

Reaction notes

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