Hydrochloric Acid → HCID 178444754, compound

HRID 1297207Notes

Reaction equation

HRID 1297207 reaction equation
C([N:8]1[C:12]([CH:13]([CH2:18][N+:19]([O-])=O)[CH2:14][CH:15]([CH3:17])[CH3:16])=[N:11][N:10]=[N:9]1)C1C=CC=CC=1.Cl>CO.[Pd]>[CH3:16][CH:15]([CH3:17])[CH2:14][CH:13]([C:12]1[NH:8][N:9]=[N:10][N:11]=1)[CH2:18][NH2:19]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69516644HCID 69516644, compound

Product 1

HCID 178444754HCID 178444754, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of 1-benzyl-5-(3-methyl-1-nitromethyl-butyl)-1H-tetrazole (1.41 g, 4.87 mmol) in MeOH (50 mL) was added 20% Pd/C (0.20 g) and concentrated HCl (0.6 g). The mixture was hydrogenated in a Parr shaker at 48 psi for 70 h, filtered, and concentrated. The residue was dissolved in 5 mL H2O and loaded onto a plug of DOWEX-50WX4-100 ion exchange resin. The column was eluted first with 100 mL H2O, then 50 mL 5% NH4OH (aq), and finally with 50 mL 10% NH4OH aq). The alkaline fractions were concentrated, and the solid obtained was dissolved in the minimum amount of MeOH. The solid was precipitated from MeOH with EtOAc, the solvent was withdrawn with a pipet, and the solid was then triturated with hot EtOAc. The solvent was drawn off with a pipet upon cooling and the remaining solid dried under vacuum to provide 0.33 g (40%) of 4-methyl-2-(1H-tetrazol-5-yl)-pentylamine as a colorless solid, mp>240° C. (dec). 1H NMR (D2O) δ 3.31 (m, 1H, —CHCH2NH2), 3.10 (m, 2H, —CH2NH2), 1.53 (m, 1H, —CHCHHCH—), 1.35 (m, 1H, —CHCHHCH—), 1.03 (m, 1H, CH3CH—), 0.66 (d, J=6.6 Hz, 3H, CH3—), 0.61 (d, J=6.6 Hz, 3H, CH3—). LRMS: m/z 168.0 (M−1). Anal. Calcd for C7H15N5: C, 49.68; H, 8.93; N, 41.38. Found: C, 49.51; H, 8.90; N, 41.20.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in 5 mL H2O
  4. washThe column was eluted first with 100 mL H2O
  5. concentrationThe alkaline fractions were concentrated
  6. customthe solid obtained
  7. customThe solid was precipitated from MeOH with EtOAc
  8. customthe solvent was withdrawn with a pipet
  9. customthe solid was then triturated with hot EtOAc
  10. temperatureupon cooling
  11. customthe remaining solid dried under vacuum

Sources & evidence

ORD record
ord-177f77a304b74344921fb790a02bd6cc
Source dataset
uspto-grants-2007_07
Patent number
US07250433B2

Reaction notes

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