Hydrochloric Acid → 5-methyl-4-(methylamino)methyl-1-triphenylmethyl-1H-imidazole

HRID 1494427Notes

Reaction equation

HRID 1494427 reaction equation
[CH3:1][C:2]1[N:6]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[N:4][C:3]=1[CH:26]=O.Cl.CN.[C:31]([BH3-])#[N:32].[Na+].Cl.C(=O)([O-])[O-].[K+].[K+]>CO.O>[CH3:31][NH:32][CH2:26][C:3]1[N:4]=[CH:5][N:6]([C:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:2]=1[CH3:1]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 118243385-methyl-1-trityl-1H-imidazole-4-carbaldehyde

Product 1

HCID 153083055-methyl-4-(methylamino)methyl-1-triphenylmethyl-1H-imidazoleYield 104.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 5-methyl-1-(triphenylmethyl)-1H-imidazole-4-carboxaldehyde (3.2 g) and methylamine hydrochloride (3.6 g) in methanol (60 ml) was stirred at room temperature for 1h. The mixture was then cooled to 0°, treated with sodium cyanoborohydride (0.62 g) for 2h and water (40 ml) was added. The resulting mixture was then stirred at 20° for 0.5h, cooled to 0° and treated with concentrated hydrochloric acid (10 ml). The mixture was then allowed to warm to 20°, and stirred at 20 for a further 1h and basified (to pH9) with potassium carbonate. The alkaline aqueous mixture was diluted with water (100 ml) and extracted with ethyl acetate (×200 ml). The combined organic extracts were dried and evaporated to leave a foam (3.5 g) which was purified by FCC eluting with System A (100:8:1) to give the title compound (1.8 g) as a solid, t.l.c. (System A, 100:3:1) Rf 0.1.

Workup

  1. temperatureThe mixture was then cooled to 0°
  2. additionwas added
  3. temperaturecooled to 0°
  4. temperatureto warm to 20°
  5. extractionextracted with ethyl acetate (×200 ml)
  6. customThe combined organic extracts were dried
  7. customevaporated

Sources & evidence

ORD record
ord-2f63e2a9671140138ec164505c5e9aaf
Source dataset
uspto-grants-1991_06
Patent number
US05026722

Reaction notes

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