Dimethylamine → HCID 21514639, compound

HRID 267479Notes

Reaction equation

HRID 267479 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].C1(C)C=CC(S(O)(=O)=O)=CC=1>[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

5

Reactant 3

HCID 674DimethylamineHCID 6101p-Toluenesulfonic acidHCID 21514640HCID 21514640, compound

Product 1

HCID 21514639HCID 21514639, compound

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

To a mixture of 201 parts (1 mole) of N-(1,1-dimethyl-3-oxobutyl)-3-methoxypropionamide and 91 parts (2 moles) of dimethylamine are added 0.5 part of platinum oxide and 3 parts of p-toluenesulfonic acid. The liquid mixture is poured into a hydrogenation bottle, flushed with hydrogen and pressurized with hydrogen on a Parr hydrogenation apparatus at 69 psi. and hydrogenated for about 12 hours, with hydrogen pressure being replenished to 70 psi. when it has dropped to 27 psi. The mixture is then stripped on a rotary evaporator and the residue, a yellow liquid, is dissolved in 16% aqueous hydrochloric acid and extracted with four 100-ml. portions of chloroform. The aqueous solution is then made alkaline by the addition of a solution of 30 parts of sodium hydroxide in 75 parts of water, the alkaline solution is again extracted with four 100-ml. portions of chloroform and the chloroform extracts are stripped and distilled. The desired product, N-(1,1-dimethyl-3-dimethylaminobutyl)-3-methoxypropionamide, is obtained boiling at 87°-95° C./0.5 mm. It contains 12.1% nitrogen, as compared with 12.2% theoretical.

Workup

  1. additionThe liquid mixture is poured into a hydrogenation bottle
  2. customflushed with hydrogen
  3. additionwhen it has dropped to 27 psi
  4. customThe mixture is then stripped on a rotary evaporator
  5. dissolutionthe residue, a yellow liquid, is dissolved in 16% aqueous hydrochloric acid
  6. extractionextracted with four 100-ml
  7. additionby the addition of a solution of 30 parts of sodium hydroxide in 75 parts of water
  8. extractionthe alkaline solution is again extracted with four 100-ml
  9. distillationdistilled

Sources & evidence

ORD record
ord-05f7918a48ff4a0da9f8870f8414d0ea
Source dataset
uspto-grants-1976_03
Patent number
US03943114

Reaction notes

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