Methane → HCID 6516121, compound

HRID 1198631Notes

Reaction equation

HRID 1198631 reaction equation
[ClH:1].[CH3:2][NH:3][CH3:4].[CH2:5]=O.[CH:7](=[C:12]1/[C:13](=[O:17])[CH2:14][CH2:15][CH2:16]/1)\[CH2:8][CH2:9][CH2:10][CH3:11].C>Cl.C(O)C>[ClH:1].[CH3:2][N:3]([CH2:5][CH:14]1[CH2:15][CH2:16]/[C:12](=[CH:7]\[CH2:8][CH2:9][CH2:10][CH3:11])/[C:13]1=[O:17])[CH3:4]

Participants

7

Reactant 4

HCID 297MethaneHCID 712Formaldehyde2×HCID 10473Dimethylamine, hydrochlorideHCID 1621050(2E)-2-Pentylidenecyclopentanone

Product 1

HCID 6516121HCID 6516121, compoundYield 62.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

4.1 g of dimethylamine hydrochloride, 3.7 g of paraformaldehyde and 20 ml of ethanol were added with 5 drops of concentrated hydrochloric acid to 7.6 g of 2-(E)-pentylidene cyclopentanone. After refluxing for about 2 hours, the resulting solution was mixed with 2.2 g of paraformaldehyde and then refluxed for about 2 additional hours. The solution was treated with activated charcoal and filtered. The filtrate was allowed to stand overnight, filtered and washed with cold ether containing a small amount of absolute ethanol to give 7.7 g of 2-Dimethylaminomethyl-5-(E)-pentylidene cyclopentanone hydrochloride as colorless leaflets. The melting point of the product was determined to be 156°-157° C.

Workup

  1. temperatureAfter refluxing for about 2 hours
  2. temperaturerefluxed for about 2 additional hours
  3. filtrationfiltered
  4. filtrationfiltered
  5. washwashed with cold ether containing a small amount of absolute ethanol

Sources & evidence

ORD record
ord-b311e0050dd54ed5a338012d8709dc11
Source dataset
uspto-grants-1994_01
Patent number
US05281622

Reaction notes

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