Acetyl chloride → 1,3-Bis(acetylamino)adamantane

HRID 992161

Reaction equation

HRID 992161 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].C(N(CC)CC)C.[NH2:12][C:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][C:15]([NH2:23])([CH2:16]3)[CH2:14]1)[CH2:20]2.[O:24]1CC[CH2:26][CH2:25]1>CN(C)C=O>[C:1]([NH:12][C:13]12[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][C:15]([NH:23][C:25](=[O:24])[CH3:26])([CH2:16]3)[CH2:14]1)[CH2:20]2)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 213512Adamantane-1,3-diamine2×

Product 1

HCID 28177971,3-Bis(acetylamino)adamantaneYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

In an atmosphere of nitrogen, 22 mmole of acetyl chloride and 24 mmole of triethylamine were dissolved in 2 ml of tetrahydrofurane (THF). To the resultant solution, 10 ml of solution containing 10 mmole of 1,3-diaminoadamantane obtained by the method of Example 65 in N,N-dimethylformamide (DMF) was added and then stirred for 3 hours at 40° C. As a result, the conversion of 1,3-diaminoadamantane was 99%, and 1,3-bis(acetylamino)adamantane (yield 95%) was formed.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-dda9b35d9b2e4a14a9ebecad2e5bca03
Source dataset
uspto-grants-2002_10
Patent number
US06468487B1

Linked notes

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