1-Bromopropane → HCID 20230785, compound

HRID 2290907Notes

Reaction equation

HRID 2290907 reaction equation
[H-].[Na+].[ClH:3].[CH3:4][O:5][C:6]1[C:18]2[CH2:17][CH2:16][CH:15]3[CH:11]([CH2:12][NH:13][CH2:14]3)[C:10]=2[CH:9]=[CH:8][C:7]=1[O:19][CH3:20].Br[CH2:22][CH2:23][CH3:24]>CN(C=O)C>[ClH:3].[CH2:22]([N:13]1[CH2:12][CH:11]2[CH:15]([CH2:16][CH2:17][C:18]3[C:6]([O:5][CH3:4])=[C:7]([O:19][CH3:20])[CH:8]=[CH:9][C:10]=32)[CH2:14]1)[CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 20230765HCID 20230765, compound

Product 1

HCID 20230785HCID 20230785, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A slurry of NaH (0.68 g, 50% in oil, 14.1 mmole, washed 3 times with hexane) and 68 mL dry DMF was stirred under N2 at room temperature as a solution of the compound of example 5 (free base) (3.0 g, 12.9 mmole) in 20 mL dry DMF was added dropwise. The reaction mixture was stirred for 1.5 hr. at room temperature, then 1-bromopropane (1.3 mL, 14.1 mmole) was added dropwise. The reaction mixture was stirred for 1 hr at room temperature, and for 18 hrs. at 30°-35° C. The reaction mixture was evaporated to dryness, water was added and the solution was extracted 3 times with CH2Cl2. The combined CH2Cl2 layers were washed with water, brine, dried (MgSO4), filtered, evaporated, and converted to the HCl salt to yield 2.0 g (50%) gray glass; M+ 246.

Workup

  1. additionwas added dropwise
  2. stirringThe reaction mixture was stirred for 1 hr at room temperature
  3. waitfor 18 hrs
  4. customat 30°-35° C
  5. customThe reaction mixture was evaporated to dryness, water
  6. additionwas added
  7. extractionthe solution was extracted 3 times with CH2Cl2
  8. washThe combined CH2Cl2 layers were washed with water, brine
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-e4972be29db04445921723a121888171
Source dataset
uspto-grants-1986_10
Patent number
US04618683

Reaction notes

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