Hydrochloric Acid → HCID 20261507, compound

HRID 465051Notes

Reaction equation

HRID 465051 reaction equation
[N-]=[N+]=[N-].O.[CH2:5]([N:7]([CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][C:12]1=[O:17])[CH2:8][CH3:9])[CH3:6].[N-:18]=[N+]=[N-].[Na+].[ClH:22]>C(OCC)(=O)C.CO>[ClH:22].[CH2:5]([N:7]([CH2:10][CH:11]1[NH:18][C:12](=[O:17])[CH2:13][CH2:14][CH2:15][CH2:16]1)[CH2:8][CH3:9])[CH3:6]

Participants

7

Reactant 5

HCID 313Hydrochloric Acid3×HCID 962WaterHCID 33557Sodium AzideHCID 33558AzideHCID 415449HCID 415449, compound

Product 1

HCID 20261507HCID 20261507, compound

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

While maintaining a reaction temperature of from -10° to -5° C., a solution azide (10.0 g, 0.154 mol) in as little water as possible is added dropwise to a solution of 2-[(diethylamino)methyl]-cyclohexanone (22.0 g, 0.1 mol) in concentrated hydrochloric acid (200 ml). After the cooling has been stopped, the mixture is stirred (48 minutes) at ambient temperature. After further cooling to -10° to -5° C., sodium azide, (5.0 g, 0.77 mol) is added in the same way as described above, after which the mixture is stirred for a further 24 hours at ambient temperature. Then, the reaction mixture is concentrated under water jet vacuum, the syrupy residue is taken up in 10 ml of water, mixed with substantially anhydrous sodium carbonate and stirred thoroughly with ethyl acetate (200 ml). After removal of the solvent the organic phase leaves an oily residue which can be converted into a hydrochloride by treatment with ethereal hydrogen chloride solution. M.p. 171° C. (ethyl acetate/methanol 3:1 v/v). Yield: 10.1 g.

Workup

  1. temperatureWhile maintaining a reaction temperature of from -10° to -5° C.
  2. temperatureAfter further cooling to -10° to -5° C.
  3. stirringis stirred for a further 24 hours at ambient temperature
  4. concentrationThen, the reaction mixture is concentrated under water jet vacuum
  5. additionmixed with substantially anhydrous sodium carbonate
  6. stirringstirred thoroughly with ethyl acetate (200 ml)
  7. customAfter removal of the solvent the organic phase
  8. customleaves an oily residue which

Sources & evidence

ORD record
ord-497dafa86ac841628fa4bcd9f6bb798b
Source dataset
uspto-grants-1985_10
Patent number
US04550107

Reaction notes

Loading…