Dimethylamine → HCID 18410501, compound

HRID 992160

Reaction equation

HRID 992160 reaction equation
C(Cl)(=O)C.[CH3:5][NH:6][CH3:7].[C:8]([C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][C:13]([N+:21]([O-:23])=[O:22])([CH2:14]3)[CH2:12]1)[CH2:18]2)(O)=[O:9]>CN(C=O)C>[CH3:5][N:6]([CH3:7])[C:8]([C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][C:13]([N+:21]([O-:23])=[O:22])([CH2:14]3)[CH2:12]1)[CH2:18]2)=[O:9]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 6367Acetyl chlorideHCID 392393-Nitrotricyclo(3.3.1.13,7)decane-1-carboxylic acid

Product 1

HCID 18410501HCID 18410501, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an atmosphere of nitrogen, 10 mmole of 1-carboxy-3-nitroadamantane obtained by the method of Example 43 was dissolved in 10 ml of DMF. To the mixture, 15 mmole of acetyl chloride was added dropwise over 30 minutes. The mixture was heated to begin to reflux around the conclusion of the addition. After refluxing for 2 hours, the mixture was cooled,and 25 mmole of dimethylamine was added dropwise over 30 minutes while retaining the temperature of the mixture at 10° C. or less followed by stirring for more 2 hours. As a result, the conversion of 1-carboxy-3-nitroadamantane was 99%, and 1-(N,N-dimethylcarbamoyl)-3-nitroadamantane (yield 95%) was formed.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux around the conclusion of the addition
  3. temperatureAfter refluxing for 2 hours
  4. additionwas added dropwise over 30 minutes
  5. customat 10° C. or less

Sources & evidence

ORD record
ord-01f4e1c48de94dbfac23ea147987f5e6
Source dataset
uspto-grants-2002_10
Patent number
US06468487B1

Linked notes

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