Triethylamine → HCID 21994061, compound

HRID 1978373Notes

Reaction equation

HRID 1978373 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Br[CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(OCC)(=O)C>C(O)C>[C:26]1([CH2:25][CH2:24][CH2:23][N:11]2[CH2:12][CH2:13][CH2:14][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 8857Ethyl AcetateHCID 12503(3-Bromopropyl)benzene2×HCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 21994061HCID 21994061, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4.50 g (22.47 mmol.) of 1-tert-butoxycarbonyl-2,3,5,6-tetrahydro-7H-1,4-diazepine in ethanol (50 ml) were added, at room temperature, 4.7 ml (33.72 mmol.) of triethylamine and 4.47 g (22.45 mmol.) of 1-bromo-3-phenylpropane. The mixture was heated under reflux for 8 hours under nitrogen atmosphere. To the reaction system were further added 4.7 ml (33.72 mmol.) of triethylamine and 4.47 g (22.45 mmol.) of 1-bromo-3-phenylpropane. The mixture was heated for 16 hours under reflux, which was cooled to room temperature. To the reaction system was added ethyl acetate, which was washed with water and a saturated aqueous saline solution, followed by drying over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by means of a column chromatography. The solvent was distilled off under reduced pressure to give the object compound as a yellow liquid product. The yield was 5.41 g (76%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 8 hours under nitrogen atmosphere
  3. temperatureThe mixture was heated for 16 hours
  4. temperatureunder reflux
  5. washwas washed with water
  6. dry with materialby drying over magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was purified by means of a column chromatography
  9. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-be9e4f1ac010422a8bd77a2783a151c2
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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