Diisopropylethylamine → CH3CN NH4OH

HRID 1700172Notes

Reaction equation

HRID 1700172 reaction equation
Cl.Cl.[CH3:3][N:4]1[CH:8]=[C:7]([CH2:9][CH2:10][NH2:11])[N:6]=[CH:5]1.[F:12][C:13]1[CH:20]=[C:19]([CH:21]=[O:22])[CH:18]=[CH:17][C:14]=1[C:15]#[N:16].[CH:23]([N:26](C(C)C)CC)(C)[CH3:24]>>[F:12][C:13]1[CH:20]=[C:19]([CH:21]2[C:8]3[N:4]([CH3:3])[CH:5]=[N:6][C:7]=3[CH2:9][CH2:10][NH:11]2)[CH:18]=[CH:17][C:14]=1[C:15]#[N:16].[NH4+:26].[OH-:22].[CH3:24][C:23]#[N:26]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 112173392-Fluoro-4-formylbenzonitrileHCID 119576011-Methylhistamine dihydrochloride

Product 2

HCID 183178222-Fluoro-4-(3-methyl-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridin-4-yl)-benzonitrileHCID 19098099CH3CN NH4OHYield 0%

Conditions

Temperature
125 °C

Procedure

2(1-Methyl-1H-imidazol-4-yl)-ethylamine bis hydrochloride (0.15 g, 0.757 mmol), 2-fluoro-4-formyl-benzonitrile (0.112 g, 0.757 mmol), prepared as described in Step D, and diisopropylethylamine (0.40 mL, 2.30 mmol) were heated at 125° C. for 1 h. The reaction mixture was concentrated in vacuo, partitioned between CH2Cl2 and saturated NaHCO3 solution, the aqueous layer extracted with CH2Cl2 (2×), the organic layers combined, dried (Na2SO4), filtered and concentrated to give the title compound after chromatography on SiO2 eluting with 0-3% NH4OH/CH3CN.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned between CH2Cl2 and saturated NaHCO3 solution
  3. extractionthe aqueous layer extracted with CH2Cl2 (2×)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bea530514280492bbb4215b4227520a2
Source dataset
uspto-grants-2002_02
Patent number
US06350755B1

Reaction notes

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