Bicyclo[2.2.2]octan-1-amine hydrochloride → 4-Aminobicyclo(2.2.2)octane

HRID 72361Notes

Reaction equation

HRID 72361 reaction equation
CC1(C)C(C)(C)OC(OC2C=CC([N+]([O-])=O)=CC=2)=NS1(=O)=O.Cl.[NH2:24][C:25]12[CH2:32][CH2:31][CH:28]([CH2:29][CH2:30]1)[CH2:27][CH2:26]2>ClCCl.C(N(CC)C(C)C)(C)C>[NH2:24][C:25]12[CH2:32][CH2:31][CH:28]([CH2:29][CH2:30]1)[CH2:27][CH2:26]2

Participants

5

Reactant 2

HCID 13182386Bicyclo[2.2.2]octan-1-amine hydrochlorideHCID 718136815,5,6,6-Tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

Product 1

HCID 5502144-Aminobicyclo(2.2.2)octaneYield 131.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Procedure

300 mg of 5,5,6,6-tetramethyl-2-(4-nitrophenoxy)-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide and 163 mg of 1-aminobicyclo[2.2.2]octane hydrochloride were dissolved in a mixture of 5 ml of dichloromethane and 0.38 ml of N,N-diisopropylethylamine, and the mixture was stirred at room temperature for 72 hours. Subsequently, the reaction solution was concentrated by rotary evaporation and the residue was purified in a purification laboratory by means of preparative HPLC. After lyophilization of the product-containing fractions, the product (166 mg) was thus obtained with a molecular weight of 314.5 g/mol (C15H26N2O3S); MS (ESI): m/e=315 (M+H+).

Workup

  1. concentrationSubsequently, the reaction solution was concentrated by rotary evaporation
  2. customthe residue was purified in a purification laboratory by means of preparative HPLC

Sources & evidence

ORD record
ord-d4a98dcfb154461491d3987b0d25636b
Source dataset
uspto-grants-2014_09
Patent number
US08828994B2

Reaction notes

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