Dichloromethane → HCID 18933338, compound

HRID 1598384Notes

Reaction equation

HRID 1598384 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:10][CH2:11][CH2:12][N:13]2C(=O)C3=CC=CC=C3C2=O)=[CH:4][CH:3]=1.O.NN.ClCCl>CO>[NH2:13][CH2:12][CH2:11][CH2:10][N:9]([CH2:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[C:24](=[O:25])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24654Hydrazine hydrate (1:1)HCID 18933441HCID 18933441, compound

Product 1

HCID 18933338HCID 18933338, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[5-(p-fluorophenyl)-4-(tert-butoxycarbonyl)-4-azapentyl]phthalimide (2.1 g, 5.1 mmol) in methanol (20 ml) was added hydrazine monohydrate (0.4 ml) and the mixture was heated under reflux for 3 hours. After cooling, to the reaction mixture was added dichloromethane (50 ml) and then washed with aqueous ammonia (50 ml×2). The organic layer was dried over anhydrous potassium carbonate and the solvent was distilled off under reduced pressure to give 1.2 g of the title compound as a colorless oily substance. Yield=85%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling, to the reaction mixture
  4. washwashed with aqueous ammonia (50 ml×2)
  5. dry with materialThe organic layer was dried over anhydrous potassium carbonate
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d2f653b6b90e42d0b3d3af4f922056d3
Source dataset
uspto-grants-1998_04
Patent number
US05736550

Reaction notes

Loading…