Triethylamine → HCID 9949458, compound

HRID 1386932Notes

Reaction equation

HRID 1386932 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:13][C:12]([C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[CH2:17][NH2:18])=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH2:22](N(CC)CC)C.ClC(OCC)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:13][C:12]([C:14]3[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=3)[CH2:17][NH:18][CH3:22])=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 9861789HCID 9861789, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9949458HCID 9949458, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-[2-(3,4-dichloro-phenyl)-3H-imidazol-4-yl]-benzylamine (1.59 g, 5.0 mmol) and triethylamine (1.01 g, 10.0 mmol) in THF (32 ml) was cooled in an ice bath and treated with a solution of ethyl chloroformate (1.08 g, 10 mmol) in THF (10 ml). The resulting mixture was stirred at r.t. for 1 hr., filtered, treated with 1.14 g (30 mmol) lithium aluminum hydride and refluxed for 2 hrs. Then saturated Seignette-salt solution (6 ml) was added slowly and stirring was continued for 30 min. The precipitate was filtered and the organic phase evaporated and chromatographed over SiO2 with CH2Cl2—CH3OH—NH4OH (200:10:1) to obtain {3-[2-(3,4-dichloro-phenyl)-3H-imidazol-4-yl]-benzyl}-methyl-amine (0.91 g, 55%) as an oil which after HCl/MeOH addition was crystallized as a light yellow hydrochloride salt. Mp. 145° C. (dec.) (MeOH/Ipr2O), MS: m/e=332 (M+H+).

Workup

  1. filtration, filtered
  2. temperaturerefluxed for 2 hrs
  3. stirringstirring
  4. waitwas continued for 30 min
  5. filtrationThe precipitate was filtered
  6. customthe organic phase evaporated
  7. customchromatographed over SiO2 with CH2Cl2—CH3OH—NH4OH (200:10:1)

Sources & evidence

ORD record
ord-c5c91c9c00eb44e9a0474f0573a16cd1
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

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