Hydrazine hydrate (1:1) → 1-(4-chlorophenyl)-2-(1-trityl-1H-imidazol-2-yl)ethanamine

HRID 423100Notes

Reaction equation

HRID 423100 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:34]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:9][C:10]2[N:11]([C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=[CH:13][N:14]=2)=[CH:4][CH:3]=1.O.NN>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH2:34])[CH2:9][C:10]2[N:11]([C:15]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=[CH:13][N:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 577504122-(1-(4-chlorophenyl)-2-(1-trityl-1H-imidazol-2-yl)ethyl)isoindoline-1,3-dione2×

Product 1

HCID 577504101-(4-chlorophenyl)-2-(1-trityl-1H-imidazol-2-yl)ethanamineYield 67.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(1-(4-chlorophenyl)-2-(1-trityl-1H-imidazol-2-yl)ethyl)isoindoline-1,3-dione (Intermediate 87) (1.78 g, 3.00 mmol) and hydrazine hydrate (0.204 mL, 4.19 mmol) in methanol (30 mL) were refluxed for 3 hours. The resulting clear solution was left to cool to room temperature overnight then filtered. The filtrate was applied to a 20 g SCX cartridge and eluted with methanol followed by 2N NH3(MeOH). Product-containing fractions were combined and concentrated by evaporation then purified by flash silica chromatography, elution gradient 2 to 5% MeOH in DCM. Pure fractions were evaporated to dryness to afford 1-(4-chlorophenyl)-2-(1-trityl-1H-imidazol-2-yl)ethanamine (0.942 g, 67.8%) as a colourless solid.

Workup

  1. waitThe resulting clear solution was left
  2. filtrationthen filtered
  3. washeluted with methanol
  4. concentrationconcentrated by evaporation
  5. customthen purified by flash silica chromatography, elution gradient 2 to 5% MeOH in DCM
  6. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-00adb6617adc43daa3559a7b0784816f
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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