Hydrochloric Acid → HCID 178510902, compound

HRID 1297212Notes

Reaction equation

HRID 1297212 reaction equation
[C:1]1(=[C:6]([C:9]2[N:10]=[N:11][N:12](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:13]=2)[C:7]#[N:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl>CO.C1COCC1.O=[Pt]=O>[CH:1]1([CH:6]([C:9]2[NH:13][N:12]=[N:11][N:10]=2)[CH2:7][NH2:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69516114HCID 69516114, compound

Product 1

HCID 178510902HCID 178510902, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of cyclopentylidene-(2-trityl-2H-tetrazol-5-yl)-acetonitrile (2.05 g, 4.91 mmol) in 50 mL MeOH:THF (1:1) was added PtO2 (0.2 g), concentrated HCl (1.49 g), and the mixture was hydrogenated in a Parr shaker at 48 psi for 8 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 0.54 g (61%) of 2-cyclopentyl-2-(1H-tetrazol-5-yl)-ethylamine as a colorless solid. 1H NMR (D2O) δ 3.22 (m, 2H, —CH2NH2), 3.06 (m, 1H, —CHCH2NH2), 1.99 (m, 1H, —CHCHCH2NH2), 1.72 (m, 1H), 1.03-1.38 (m, 6H), 0.87 (m, 1H). 13C NMR (CD3OD) □ 161.11, 42.78, 42.56, 40.48, 30.61, 30.11, 24.96, 24.53. LRMS: m/z 180.1 (M−1). Anal. Calc'd for C8H15N5: C, 53.02; H, 8.34; N, 38.64. Found: C, 51.59; H, 8.18; N, 37.96.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-421a1cdcd88d44328613329db24ee680
Source dataset
uspto-grants-2007_07
Patent number
US07250433B2

Reaction notes

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