Dimethylamine, hydrochloride → N,N-dimethyl-2-[(5,6-dichloro-9a-propyl-3-oxo-2,3,9,9a-tetrahydro-1H-fluoren-7-yl)oxy]ethanimidamide hydrochloride hemihydrate

HRID 364012

Reaction equation

HRID 364012 reaction equation
[Na].[Cl:2][C:3]1[C:15]([Cl:16])=[C:14]([O:17][CH2:18][C:19]#[N:20])[CH:13]=[C:12]2[C:4]=1[C:5]1[C:10]([CH2:21][CH2:22][CH3:23])([CH2:11]2)[CH2:9][CH2:8][C:7](=[O:24])[CH:6]=1.[ClH:25].[CH3:26][NH:27][CH3:28]>CO>[OH2:17].[ClH:2].[CH3:26][N:27]([CH3:28])[C:19](=[NH:20])[CH2:18][O:17][C:14]1[CH:13]=[C:12]2[C:4]([C:5]3[C:10]([CH2:21][CH2:22][CH3:23])([CH2:11]2)[CH2:9][CH2:8][C:7](=[O:24])[CH:6]=3)=[C:3]([Cl:25])[C:15]=1[Cl:16].[CH3:26][N:27]([CH3:28])[C:19](=[NH:20])[CH2:18][O:17][C:14]1[CH:13]=[C:12]2[C:4]([C:5]3[C:10]([CH2:21][CH2:22][CH3:23])([CH2:11]2)[CH2:9][CH2:8][C:7](=[O:24])[CH:6]=3)=[C:3]([Cl:25])[C:15]=1[Cl:16].[ClH:2]

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 5360545SodiumHCID 13686916[(5,6-dichloro-2,3,9,9a-tetrahydro-3-oxo-9a-propyl-1H-fluoren-7-yl)oxy]acetonitrile

Product 1

HCID 131714796N,N-dimethyl-2-[(5,6-dichloro-9a-propyl-3-oxo-2,3,9,9a-tetrahydro-1H-fluoren-7-yl)oxy]ethanimidamide hydrochloride hemihydrate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium metal (20 mg) in methanol (30 ml) was added the R(+)-enantiomer of [(5,6-dichloro-2,3,9,9a-tetrahydro-3-oxo-9a-propyl-1H-fluoren-7-yl)oxy]acetonitrile (1.0 g, 2.9 mMole). The reaction mixture was stirred for 1-1/2 hours in a dry nitrogen atmosphere then treated with dimethylamine hydrochloride (475 mg, 5.8 mMole) and stirring was continued for 21/2 hours. The methanol was evaporated in vacuo, the residue was dissolved in water, treated with 10N NaOH (1 ml), extracted with diethyl ether containing 10% tetrahydrofuran, washed with water and brine, dried over potassium carbonate and evaporated in vacuo. The residue was dissolved in a mixture of ethanol and diethyl ether, treated with ethanolic HCl, filtered under nitrogen and washed with diethyl ether to give 0.8 g of the R(+)-enantiomer of N,N-dimethyl-2-[(5,6-dichloro-9a-propyl-3-oxo-2,3,9,9a-tetrahydro-1H-fluoren-7-yl)oxy]ethanimidamide hydrochloride hemihydrate.

Workup

  1. stirringstirring
  2. custom2 hours
  3. customThe methanol was evaporated in vacuo
  4. dissolutionthe residue was dissolved in water
  5. additiontreated with 10N NaOH (1 ml)
  6. extractionextracted with diethyl ether containing 10% tetrahydrofuran
  7. washwashed with water and brine
  8. dry with materialdried over potassium carbonate
  9. customevaporated in vacuo
  10. dissolutionThe residue was dissolved in a mixture of ethanol and diethyl ether
  11. additiontreated with ethanolic HCl
  12. filtrationfiltered under nitrogen
  13. washwashed with diethyl ether

Sources & evidence

ORD record
ord-1dfdb3c2c4b34ca48f4a0940c17c408c
Source dataset
uspto-grants-1986_08
Patent number
US04604396

Linked notes

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