4-(2-Bromoethoxy)benzonitrile → HCID 69843550, compound

HRID 1596477Notes

Reaction equation

HRID 1596477 reaction equation
[CH:1]12[CH2:9][CH:5]([CH2:6][NH:7][CH2:8]1)[CH2:4][N:3]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:2]2.Br[CH2:18][CH2:19][O:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1>CC#N>[C:13]([O:12][C:10]([N:3]1[CH2:2][CH:1]2[CH2:9][CH:5]([CH2:6][N:7]([CH2:18][CH2:19][O:20][C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=3)[CH2:8]2)[CH2:4]1)=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 24522124-(2-Bromoethoxy)benzonitrileHCID 22490264Tert-butyl 3,7-diazabicyclo(3.3.1)nonane-3-carboxylate

Product 1

HCID 69843550HCID 69843550, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

tert-Butyl-3,7-diazabicyclo[3.3.1]nonane-3-carboxylate (3.62 g; 16 mmol; see Example F above) was added to added to a stirred solution of 4-(2-bromoethoxy)benzonitrile (3.62g; 16 mmol; see Example 67(a) above) and TEA (3.34 mL; 24 mmol) in MeCN (70 mL) and the reaction mixture was stirred at 60° C. overnight and then stored at room temperature for 48 h. The solids were filtered off, washed with IPA (2×100 mL) and the filtrate concentrated. The residue was partitioned between DCM and NaHCO3 (sat.), the organic layer was separated, dried (MgSO4) and concentrated. The oily residue was subjected to column chromatography (DCM:MeOH; 25:1) to give the title compound in a 72% yield.

Workup

  1. waitstored at room temperature for 48 h
  2. filtrationThe solids were filtered off
  3. washwashed with IPA (2×100 mL)
  4. concentrationthe filtrate concentrated
  5. customThe residue was partitioned between DCM and NaHCO3 (sat.)
  6. customthe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-27b273b26bb44580ad913fd29a4765e5
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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