Succinyl chloride → Succinic acid bis(3,4-dibenzyloxybenzylamide)

HRID 2170278Notes

Reaction equation

HRID 2170278 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:12][NH2:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:25](Cl)(=[O:31])[CH2:26][CH2:27][C:28](Cl)=[O:29]>N1C=CC=CC=1.ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:12][NH:13][C:25](=[O:31])[CH2:26][CH2:27][C:28]([NH:13][CH2:12][C:11]1[CH:14]=[CH:15][C:16]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=1)=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 10970Succinyl chlorideHCID 218216603,4-Dibenzyloxybenzylamine

Product 1

HCID 57634450Succinic acid bis(3,4-dibenzyloxybenzylamide)

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3,4-dibenzyloxybenzylamine (1.1 g, 3.45 mmol) was dissolved in anhydrous pyridine (8 ml) and cooled to 0° C. with stirring under nitrogen. To this solution, succinyl chloride (0.23 g, 1.42 mmol) was added dropwise over 30 minutes as a solution in dichloromethane (50 ml), while maintaining the reaction mixture at 0° C. The reaction was allowed to warm to room temperature and stirred for an additional 45 minutes. The reaction was poured onto crushed ice (70 g) and the dichloromethane layer was separated. The organic extract was washed with dilute aqueous hydrochloric acid (2×20 ml of 0.1M solution), water (20 ml), and dried (Na2SO4). Removal of the solvent at reduced pressure afforded a crude solid, which was triturated with methanol (5 ml) to afford after filtration the protected diamide, yield 300 mg.

Workup

  1. temperaturewhile maintaining the reaction mixture at 0° C
  2. temperatureto warm to room temperature
  3. stirringstirred for an additional 45 minutes
  4. additionThe reaction was poured
  5. customthe dichloromethane layer was separated
  6. extractionThe organic extract
  7. washwas washed with dilute aqueous hydrochloric acid (2×20 ml of 0.1M solution), water (20 ml)
  8. dry with materialdried (Na2SO4)
  9. customRemoval of the solvent at reduced pressure
  10. customafforded a crude solid, which
  11. customwas triturated with methanol (5 ml)
  12. customto afford
  13. filtrationafter filtration the protected diamide, yield 300 mg

Sources & evidence

ORD record
ord-16379f0dd05d477582a807f2a5ea2a8e
Source dataset
uspto-grants-2015_06
Patent number
US09051253B2

Reaction notes

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