Hydrochloric Acid → HCID 178443396, compound

HRID 1297210Notes

Reaction equation

HRID 1297210 reaction equation
[CH2:1]([CH:4]([CH2:33][CH2:34][CH3:35])[CH:5]=[C:6]([C:9]1[N:10]=[N:11][N:12](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[N:13]=1)[C:7]#[N:8])[CH2:2][CH3:3].CO.Cl>O=[Pt]=O.C1COCC1>[CH2:33]([CH:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH:6]([C:9]1[NH:13][N:12]=[N:11][N:10]=1)[CH2:7][NH2:8])[CH2:34][CH3:35]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 69517064HCID 69517064, compound

Product 1

HCID 178443396HCID 178443396, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-propyl-2-(2-trityl-2H-tetrazol-5-yl)-hept-2-enenitrile (1.60 g, 3.47 mmol) in 50 mL 1:1 MeOH:THF was added PtO2 (0.1 g), concentrated HCl (1.09 g), and the mixture was hydrogenated in a Parr shaker at 48 psi for 30 h. The mixture was filtered and concentrated. Flash chromatography of the residue on silica gel (0.25:1.25:3.5 conc. NH4OH (aq):MeOH:CH2Cl2), followed by a second column using the same conditions, provided 0.40 g (51%) of 4-propyl-2-(1H-tetrazol-5-yl)-heptylamine as a colorless solid. 1H NMR (D2O) δ 3.29 (m, 1H, —CHCH2NH2), 3.09 (m, 2H, —CH2NH2), 1.56 (m, 1H, —CHCHHCH—), 1.37 (m, 1H, —CHCHHCH—), 0.80-1.07 (m, 9H, —CH2CHCH2—, —CH2CH2—), 0.58 (t, J=6.6 Hz, 3H, CH3—), 0.47 (t, J=6.6 Hz, 3H, CH3—). Anal. Calcd for C11H23N5: C, 58.63; H, 10.29; N, 31.08. Found: C, 57.87; H, 10.04; N, 30.73.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-cc5cb40ce72c433bbe6f89a5e50caa32
Source dataset
uspto-grants-2007_07
Patent number
US07250433B2

Reaction notes

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