Dimethylamine, hydrochloride → HCID 57246587, compound

HRID 2287337Notes

Reaction equation

HRID 2287337 reaction equation
[C:1]1([CH:7]=[N:8][N:9]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17]I)[C:10]2=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:21][NH:22][CH3:23].C[O-].[Na+]>CN(C)C=O>[C:1]1([CH:7]=[N:8][N:9]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:22]([CH3:23])[CH3:21])[C:10]2=[O:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 10942334Sodium MethoxideHCID 57037835HCID 57037835, compound

Product 1

HCID 57246587HCID 57246587, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 1-phenylmethyleneamino-3-(4-iodobutyl)-2-imidazolidinone (prepared as described in Example B, Part II) (7.0 g, 0.0189 mole), dimethylformamide (125 ml), and dimethylamine hydrochloride (6.15 g, 0.075 mole) is heated on a steam bath. Sodium methoxide (4.05 g, 0.075 mole) is added portionwise over approximately 2 hours while heating. After addition, heating is continued 2 hours, then the mixture is cooled to ambient temperature. The mixture is concentrated under reduced pressure to an oily residue. This residue is suspended in saturated NaHCO3 solution. (300 ml) and extracted with CH2Cl2 (3×100 ml). The CH2Cl2 extract is washed with H2O (2×100 ml), then dried over MgSO4. The filtered solution is concentrated under reduced pressure to an oily-liquid residue, which is triturated in hexane (2×100 ml), decanted, then dried in vacuo, giving 4.6 g (0.016 mole) of 1-phenylmethyleneamino-3-[4-(dimethylamino)butyl]-2-imidazolidinone, as a solid.

Workup

  1. temperaturewhile heating
  2. additionAfter addition
  3. temperatureheating
  4. concentrationThe mixture is concentrated under reduced pressure to an oily residue
  5. extraction(300 ml) and extracted with CH2Cl2 (3×100 ml)
  6. extractionThe CH2Cl2 extract
  7. washis washed with H2O (2×100 ml)
  8. dry with materialdried over MgSO4
  9. concentrationThe filtered solution is concentrated under reduced pressure to an oily-liquid residue, which
  10. customis triturated in hexane (2×100 ml)
  11. customdecanted
  12. customdried in vacuo

Sources & evidence

ORD record
ord-a18bedcaadc046ae884adbe843ed103c
Source dataset
uspto-grants-2000_07
Patent number
US06083945

Reaction notes

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