1-Bromopropane → HCID 22137269, compound

HRID 1375151Notes

Reaction equation

HRID 1375151 reaction equation
[CH3:1][C:2]([O-])([CH3:4])[CH3:3].[K+].[NH:7]1[C:13](=[O:14])C[CH2:11][CH2:10][C:9]2[CH:15]=[CH:16][CH:17]=[CH:18][C:8]1=2.BrCCC>C1COCC1.C([Li])CCCCC.O.Cl>[CH3:1][CH:2]([CH:4]1[C:13](=[O:14])[NH:7][C:8]2[CH:18]=[CH:17][CH:16]=[CH:15][C:9]=2[CH2:10][CH2:11]1)[CH3:3]

Participants

8

Reactant 3

HCID 78401-BromopropaneHCID 2485801,3,4,5-Tetrahydro-2H-1-benzazepin-2-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 22137269HCID 22137269, compoundYield 46.2%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidCatalystHCID 962WaterCatalystHCID 178506865HCID 178506865, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

29,01 g (0,253 mol) potassium tert-butylate is suspended in 227 ml of THF and 40 g (0,249 mol) 1,3,4,5-tetrahydro-benzo[b]azepin-2-one is added in portions at a temperature of −16°. At the same temperature 140,22 g (0,50 mol) of n-hexyllithium (33% in hexane) are added over the course of 30 min. Then a solution of 34,28 g (0,276 mol) 3-bromo propane in 21,8 ml THF is added at a temperature of −16°. After the solution has been stirred for 23 hours and meanwhile was allowed to reach room temperature, 150 g of water is added dropwise while stirring and cooling with ice water. The resulting mixture is acidified with 62 g hydrochloric acid (37%), the phases are separated and the organic phase is evaporated. 150 ml dichloromethane is added to the residue, the suspension is filtered and the filter is washed with additional 60 ml dichloromethane. The solution is concentrated and the crystals which precipitated on cooling to 0° over night are filtered off. The solid is recrystallized from 94,9 g 2-propanol. 23,3 g (0,115 mol) of 4,5-dihydro-3-(2-propyl)-1H-benzo[b]azepine-2-one is obtained [46,1%, HPLC 98,4 area %].

Workup

  1. customto reach room temperature
  2. stirringwhile stirring
  3. customthe phases are separated
  4. customthe organic phase is evaporated
  5. addition150 ml dichloromethane is added to the residue
  6. filtrationthe suspension is filtered
  7. washthe filter is washed with additional 60 ml dichloromethane
  8. concentrationThe solution is concentrated
  9. customthe crystals which precipitated
  10. temperatureon cooling to 0° over night
  11. filtrationare filtered off
  12. customThe solid is recrystallized from 94,9 g 2-propanol

Sources & evidence

ORD record
ord-d49dee2864974fc08252c5f0de640a24
Source dataset
uspto-grants-2007_01
Patent number
US07166720B2

Reaction notes

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