Acetonitrile → HCID 57475890, compound

HRID 506854Notes

Reaction equation

HRID 506854 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.[CH3:10][C:11]([CH3:16])([CH3:15])[CH2:12][CH2:13][NH2:14].C(N(C(C)C)CC)(C)C.C(#N)C>ClCCl.[OH-].[Na+]>[CH3:10][C:11]([CH3:16])([CH3:15])[CH2:12][CH2:13][NH:14][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 197093,3-DimethylbutylamineHCID 767274-(2-Chloroethyl)morpholineHCID 81531Diisopropylethylamine

Product 1

HCID 57475890HCID 57475890, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

Into a microwave reactor was placed 4-(2-chloroethyl)-morpholine (1.5 g, 8.1 mmol), 3,3-dimethylbutylamine (2.2 mL, 16 mmol), diisopropylethylamine (3.1 mL, 18 mmol), and acetonitrile (30 mL). The resulting mixture was microwaved at 130° C. for 30 minutes and then diluted with dichloromethane and 1N sodium hydroxide. The layers were separated, and the organic extract was washed with brine, dried over magnesium sulfate, filtered, and concentrated to yield an orange oil. The oil was purified on a silica gel column, eluting with 15% of 10:1 (MeOH:NH4OH) in EtOAc to yield a yellow oil.

Workup

  1. customInto a microwave reactor was placed
  2. customThe resulting mixture was microwaved at 130° C. for 30 minutes
  3. customThe layers were separated
  4. extractionthe organic extract
  5. washwas washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto yield an orange oil
  10. customThe oil was purified on a silica gel column
  11. washeluting with 15% of 10:1 (MeOH:NH4OH) in EtOAc
  12. customto yield a yellow oil

Sources & evidence

ORD record
ord-9702cc8a1ba9496a8962b57ce6eaf676
Source dataset
uspto-grants-2010_08
Patent number
US07786116B2

Reaction notes

Loading…