56970-24-2 → 1-[N-(1-(4-cyanobenzyl)-5-imidazolylmethyl)amino]-3-methoxy-4-phenylbenzen

HRID 1422348Notes

Reaction equation

HRID 1422348 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([O:14][CH3:15])[CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:30]([C:32]1[CH:45]=[CH:44][C:35]([CH2:36][N:37]2[C:41]([CH:42]=O)=[CH:40][N:39]=[CH:38]2)=[CH:34][CH:33]=1)#[N:31]>ClCCCl.C(O)(=O)C>[C:30]([C:32]1[CH:33]=[CH:34][C:35]([CH2:36][N:37]2[C:41]([CH2:42][NH:1][C:2]3[CH:7]=[CH:6][C:5]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)=[C:4]([O:14][CH3:15])[CH:3]=3)=[CH:40][N:39]=[CH:38]2)=[CH:44][CH:45]=1)#[N:31]

Participants

6

Reactant 3

HCID 52177356970-24-2HCID 5049666Sodium triacetoxyborohydrideHCID 106322894-[(5-Formylimidazol-1-yl)methyl]benzonitrile

Product 1

HCID 222542671-[N-(1-(4-cyanobenzyl)-5-imidazolylmethyl)amino]-3-methoxy-4-phenylbenzen

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1-amino-3-methoxy-4-phenylbenzene in 1,2-dichloroethane at 0° C. was added 4A powdered molecular sieves and sodium triacetoxyborohydride. 1-(4-Cyanobenzyl)-5-imidazole-carboxaldehyde was added, followed by 5 drops of acetic acid. The cooling bath was removed after 5 hours, and the reaction was stirred for another 15 hours. The reaction was poured into ethyl acetate and water. The organic layer was extracted with sat. aq. NaHCO3 solution and brine, then dried (Na2SO4) and concentrated in vacuo to provide the product.

Workup

  1. customThe cooling bath was removed after 5 hours
  2. additionThe reaction was poured into ethyl acetate and water
  3. extractionThe organic layer was extracted with sat. aq. NaHCO3 solution and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto provide the product

Sources & evidence

ORD record
ord-298f6f90bc4e49bca1fb6eb25e1ea456
Source dataset
uspto-grants-2000_06
Patent number
US06080870

Reaction notes

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