Dimethylamine → HCID 21514639, compound

HRID 267480Notes

Reaction equation

HRID 267480 reaction equation
[CH3:1][C:2]([NH:8][C:9](=[O:14])[CH2:10][CH2:11][O:12][CH3:13])([CH3:7])[CH2:3][C:4](=O)[CH3:5].[CH3:15][NH:16][CH3:17].Cl([O-])(=O)(=O)=O.C[NH2+]C.[H][H].C(=O)(O)[O-].[Na+]>[Pt]=O>[CH3:1][C:2]([NH:8][C:9](=[O:14])[CH2:10][CH2:11][O:12][CH3:13])([CH3:7])[CH2:3][CH:4]([N:16]([CH3:17])[CH3:15])[CH3:5]

Participants

7

Reactant 5

HCID 674DimethylamineHCID 516892Sodium BicarbonateHCID 14786861HCID 14786861, compoundHCID 21514640HCID 21514640, compoundHCID 178418361HCID 178418361, compound3×

Product 1

HCID 21514639HCID 21514639, compound

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

A one-gallon autoclave, fitted with a stirrer, is charged with 1684 parts (8.38 moles) of N-(1,1-dimethyl-3-oxobutyl)-3-methoxypropionamide, 762 parts (16.9 moles) of dimethylamine, 1.5 parts of platinum oxide and 15 parts of dimethylammonium perchlorate. The autoclave is pressurized with hydrogen to 750 psi., and stirring is begun. Hydrogen pressure is periodically restored to 850-900 psi. and stirring is continued until hydrogen uptake has ceased. Sodium bicarbonate, 10 parts, is added to the mixture which is then stripped, acidified, extracted with chloroform, made alkaline and again extracted with chloroform as in Example 1. The chloroform extract from the alkaline solution is stripped and distilled, and the product, N-(1,1-dimethyl-3-dimethylaminobutyl)-3-methoxypropionamide, is obtained boiling at 108°C./0.9 mm. The yield is 1418.6 parts, or 73.6% of the theoretical amount.

Workup

  1. customA one-gallon autoclave, fitted with a stirrer
  2. stirringand stirring
  3. extractionextracted with chloroform
  4. extractionagain extracted with chloroform as in Example 1
  5. extractionThe chloroform extract from the alkaline solution
  6. distillationdistilled

Sources & evidence

ORD record
ord-4f591d5640eb484aa6f462f73df6805c
Source dataset
uspto-grants-1976_03
Patent number
US03943114

Reaction notes

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