Dimethylamine → HCID 22910531, compound

HRID 1380604Notes

Reaction equation

HRID 1380604 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[C:9](C)([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH3:10])=[CH:4][CH:3]=1.[CH3:19][NH:20][CH3:21].[CH2:22]=O>C(OCC)C>[CH3:19][N:20]([CH2:22][S:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[CH:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH3:10])=[CH:4][CH:3]=1)[CH3:21]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712Formaldehyde2×HCID 157024042-Methyl-2-(morpholin-4-yl)-1-(4-sulfanylphenyl)propan-1-one

Product 1

HCID 22910531HCID 22910531, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

7.7 g (0.03 mol) of 1-(4-mercaptophenyl)-2-methyl-2-morpholinopropan-1-one are treated, while being cooled in ice, with 10 ml of a 40% aqueous solution of dimethylamine. After 30 minutes at room temperature the mixture is again cooled in an ice bath, and 3 ml of a 35% aqueous solution of formaldehyde are added dropwise (≈0.038 mol of formaldehyde). The mixture is then stirred at room temperature for 60 minutes and is heated at 50° C. for a further 2 hours. After cooling, 25 ml of diethyl ether are added to the reaction mixture, the phases are separated and the aqueous phase is extracted three times with ether. After the ether solution has been washed with water it is dried over MgSO4 and evaporated in vacuo, whereupon the crude product is left as an oil (compound No. 34).

Workup

  1. temperatureis heated at 50° C. for a further 2 hours
  2. temperatureAfter cooling
  3. customthe phases are separated
  4. extractionthe aqueous phase is extracted three times with ether
  5. washAfter the ether solution has been washed with water it
  6. dry with materialis dried over MgSO4
  7. customevaporated in vacuo, whereupon the crude product
  8. waitis left as an oil (compound No. 34)

Sources & evidence

ORD record
ord-5f4a9a72df194324b2522fb2bb11c8be
Source dataset
uspto-grants-1986_04
Patent number
US04582862

Reaction notes

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