Formaldehyde → N-({1-[4-(Trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl)-2-propanamine

HRID 517754Notes

Reaction equation

HRID 517754 reaction equation
[CH3:1][CH:2]([NH2:4])[CH3:3].[CH2:5]=O.C[Si]([N:11]=[N+:12]=[N-:13])(C)C.[F:14][C:15]([F:25])([F:24])[C:16]1[CH:21]=[CH:20][C:19]([N+:22]#[C-:23])=[CH:18][CH:17]=1>CO>[F:14][C:15]([F:24])([F:25])[C:16]1[CH:17]=[CH:18][C:19]([N:22]2[C:23]([CH2:5][NH:4][CH:2]([CH3:3])[CH3:1])=[N:13][N:12]=[N:11]2)=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6363IsopropylamineHCID 78378AzidotrimethylsilaneHCID 27594124-(Trifluoromethyl)phenyl isocyanide

Product 1

HCID 62736828N-({1-[4-(Trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl)-2-propanamineYield 29.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (1-methylethyl)amine (0.077 mL, 0.900 mmol) and formaldehyde (35% aqueous) (0.067 mL, 0.9 mmol) in methanol (4 mL) was stirred at room temperature for 1.5 h before adding trimethylsilyl azide (0.155 mL, 1.170 mmol) and 4-(trifluoromethyl)phenyl isocyanide (200 mg, 1.170 mmol, Fluorochem, Old Glossop, UK). After stirring for 2 days the solution was concentrated in vacuo. The resulting residue was purified using MDAP. Fractions containing product were combined and concentrated in vacuo. The resulting solid was redissolved in MeOH and passed through a 5 g NH2 ion exchange column to give the title compound as a white solid (75 mg).

Workup

  1. concentrationwas concentrated in vacuo
  2. customThe resulting residue was purified
  3. additionFractions containing product
  4. concentrationconcentrated in vacuo
  5. dissolutionThe resulting solid was redissolved in MeOH

Sources & evidence

ORD record
ord-3e9fc6b65f2444bab3ce176080515ce7
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

Loading…