Bis(2-bromoethyl) ether → 2-Fluoro-4-[5-(2-morpholin-4-yl-ethyl)-imidazol-1-ylmethyl]-benzonitrile

HRID 379058Notes

Reaction equation

HRID 379058 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][C:6]1[N:10]([CH2:11][C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[C:14]([F:20])[CH:13]=2)[CH:9]=[N:8][CH:7]=1.Br[CH2:22][CH2:23][O:24][CH2:25][CH2:26]Br>C(#N)C.C(N(CC)CC)C>[F:20][C:14]1[CH:13]=[C:12]([CH2:11][N:10]2[C:6]([CH2:5][CH2:4][N:3]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:7][N:8]=[CH:9]2)[CH:19]=[CH:18][C:15]=1[C:16]#[N:17]

Participants

5

Reactant 2

HCID 21521Bis(2-bromoethyl) etherHCID 226271054-[5-(2-Amino-ethyl)-imidazol-1-ylmethyl]-2-fluoro-benzonitrile dihydrochloride

Product 1

HCID 216969472-Fluoro-4-[5-(2-morpholin-4-yl-ethyl)-imidazol-1-ylmethyl]-benzonitrile

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-[5-(2-amino-ethyl)-imidazol-1-ylmethyl]-2-fluoro-benzonitrile dihydrochloride (0.92 g, 0.0029 mmol) in acetonitrile (150 mL) and triethylamine (3.2 mL) was added 2-bromoethyl ether (0.839 mL, 0.0067 mmol) and the mixture was refluxed for 48 hr. The solvents were removed in uacuo and the residue was dissolved in EtOAc which was washed twice with 1M HCl (100 mL). The HCl layers were combined and adjusted to pH=9 with solid Na2CO3 and extraxcted 3 times with EtOAc. The EtOAc layers were combined and dried with brine and MgSO4. Removal of the EtOAc in vacuo yielded the title compound which was used as is in the next step.

Workup

  1. temperaturethe mixture was refluxed for 48 hr
  2. customThe solvents were removed in uacuo
  3. dissolutionthe residue was dissolved in EtOAc which
  4. washwas washed twice with 1M HCl (100 mL)
  5. dry with materialdried with brine and MgSO4
  6. customRemoval of the EtOAc in vacuo

Sources & evidence

ORD record
ord-42dc5bd007e148f297483fd574a84112
Source dataset
uspto-grants-2001_10
Patent number
US06297239B1

Reaction notes

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