Dimethylamine → HCID 18410514, compound

HRID 992165Notes

Reaction equation

HRID 992165 reaction equation
[CH3:1][NH:2][CH3:3].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1.[C:26]([C:29]12[CH2:38][CH:33]3[CH2:34][CH:35]([CH2:37][C:31]([CH2:39][OH:40])([CH2:32]3)[CH2:30]1)[CH2:36]2)(O)=[O:27]>CN(C=O)C>[OH:40][CH2:39][C:31]12[CH2:37][CH:35]3[CH2:34][CH:33]([CH2:38][C:29]([C:26](=[O:27])[N:2]([CH3:3])[CH3:1])([CH2:36]3)[CH2:30]1)[CH2:32]2

Participants

5

Reactant 3

HCID 674DimethylamineHCID 184104963-(Hydroxymethyl)tricyclo[3.3.1.13,7]decane-1-carboxylic acidHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 18410514HCID 18410514, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In an atmosphere of nitrogen, 10 mmole of 1-carboxy-3-hydroxymethyladamantane obtained by the method of Example 73 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 f or 8 hours. As a result, the conversion of 1-carboxy-3-hydroxymethyladamantane was 99%, and 1-hydroxymethyl-3-(N,N-dimethylcarbamoyl)adamantane (yield 95%) was formed.

Workup

  1. additionwere added

Sources & evidence

ORD record
ord-193f348868f94c88a680d9386474eb32
Source dataset
uspto-grants-2002_10
Patent number
US06468487B1

Reaction notes

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