1-Bromo-3-chloropropane → HCID 18924808, compound

HRID 1939903Notes

Reaction equation

HRID 1939903 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[NH:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]1=2.[H-].[Na+].Br[CH2:20][CH2:21][CH2:22][Cl:23]>CN(C)C=O>[Cl:23][CH2:22][CH2:21][CH2:20][N:8]1[C:2](=[O:1])[C:3]2[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=2[NH:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]1=2

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 2013275,10-Dihydro-11H-dibenzo(b,e)(1,4)diazepin-11-one

Product 1

HCID 18924808HCID 18924808, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepine (12.1 g, 0.058 mol, prepared as described in Synthesis, 1985, 550) in dry N,N-dimethylformamide (150 ml) kept under an atmosphere of nitrogen, sodium hydride (2.8 g, 0.069 mol, 60% dispersion in oil) was added and the reaction mixture was stirred for 1 hour. 1-Bromo-3-chloropropane (10.9 g, 0.069 mol) was slowly added and the mixture was stirred overnight. The reaction mixture was quenched with water (200 ml) and extracted with diethyl ether (2×250 ml). The combined organic extracts were washed with water (3×300 ml), dried (MgSO4) and the solvent was evaporated in vacuo. The solid was washed with heptane (100 ml), filtered off and dried, affording 11.1 g (67%) of 10-(3-chloro-propyl)-5,10-dihydro-dibenzo[b,e][1,4]diazepin-11-one.

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe reaction mixture was quenched with water (200 ml)
  3. extractionextracted with diethyl ether (2×250 ml)
  4. washThe combined organic extracts were washed with water (3×300 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated in vacuo
  7. washThe solid was washed with heptane (100 ml)
  8. filtrationfiltered off
  9. customdried

Sources & evidence

ORD record
ord-67f529f977544e8e8785cc77e2da0735
Source dataset
uspto-grants-1997_12
Patent number
US05698551

Reaction notes

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