Dimethylamine → HCID 22463573, compound

HRID 1937251Notes

Reaction equation

HRID 1937251 reaction equation
[CH3:1][NH:2][CH3:3].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.[C:26]([O:29][C:30]12[CH2:39][CH:34]3[CH2:35][CH:36]([CH2:38][C:32]([C:40]([OH:42])=O)([CH2:33]3)[CH2:31]1)[CH2:37]2)(=[O:28])[CH3:27]>CN(C=O)C>[C:26]([O:29][C:30]12[CH2:39][CH:34]3[CH2:35][CH:36]([CH2:38][C:32]([C:40](=[O:42])[N:2]([CH3:3])[CH3:1])([CH2:33]3)[CH2:31]1)[CH2:37]2)(=[O:28])[CH3:27]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 28182101-acetyloxy-3-carboxyadamantaneHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 22463573HCID 22463573, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In an atmosphere of nitrogen, 10 mmole of 1-acetyloxy-3-carboxyadamantane obtained by the above method was dissolved in 10 ml of DMF. To the mixture, 15 mmole of N,N′-carbodiimidazol in the form of powder was added in one portion. After stirring for 1 hour at the room temperature, 15 mmole of dimethylamine and 15 mmole of diazabicycloundecene were added. The mixture was heated to 100° C. and stirred for 8 hours. As a result, the conversion of 1-acetyloxy-3-carboxyadamantane was 80%, and 1-acetyloxy-3-(N,N-dimethylcarbamoyl)adamantane (yield 70%) was formed.

Workup

  1. additionwere added

Sources & evidence

ORD record
ord-813fb82744264e6cb95130afa6518fe4
Source dataset
uspto-grants-2002_05
Patent number
US06392104B1

Reaction notes

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