Hydrochloric Acid → Adamantane

HRID 1807351Notes

Reaction equation

HRID 1807351 reaction equation
[C:1]12(CN)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C1(=O)N(C(CC(O)=O)C(O)=O)C(=O)CC1.C1(=O)N(C(CC(O)=O)C(O)=O)C(=O)CC1.C(O)CO.Cl>ClCCl>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 53470898Ethylene glycol bis[succinimidylsuccinate]

Product 1

HCID 9238AdamantaneYield 175.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Adamantanemethylamine (0.152 g, 0.92 mmol, Aldrich, Milwaukee, Wis.) was added to Ethylene glycol bis[succinimidylsuccinate] (EGS) (0.2 g, 0.43 mmol, Pierce, Rockford, Ill.) in solution in 10 mL of anhydrous dichloromethane. The resulting solution was stirred for 5 h at room temperature. It was then acidified with 0.1 N HCl and extracted with dichloromethane. The organic phase was dried with MgSO4 and then concentrated to dryness under vacuum. This afforded 0.22 g of solid (yield 90%).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase was dried with MgSO4
  3. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-696aba0924f648338fdd428a28afcdc1
Source dataset
uspto-grants-2013_01
Patent number
US08357377B2

Reaction notes

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