Carbon Dioxide → N-Dodecyl-N-methylbenzenemethanamine

HRID 262940Notes

Reaction equation

HRID 262940 reaction equation
C(O)=O.[CH2:4]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C=O.[C:26](=O)=O.Cl.[OH-].[Na+]>O>[CH3:26][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

8

Reactant 6

HCID 280Carbon Dioxide2×HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 232909N-Benzyldodecan-1-amine

Product 1

HCID 225125N-Dodecyl-N-methylbenzenemethanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To 8.96 g (0.105 mol.) of commercial formic acid (85~90%) which was cooled by cold water was gradually added 9.5 g (0.035 mol.) of N-benzyl-n-dodecylamine. Then 2.4 ml (0.0525 mol.) of formaldehyde (37%) was added to the mixture and heated at 90°~100° C. After several minutes, carbon dioxide gas generated, during which the mixture was cooled to room temperature. When the evolution of carbon dioxide stopped, the mixture was again refluxed at 90°~100° C. for 8 hours. After completing the reaction, 18 ml of 4 N-hydrochloric acid was added to the cooled reaction mixture, which was condensed to dryness under reduced pressure. The residue was dissolved in 5 ml of water. 10 ml of 18N-sodium hydroxide solution was added to the aqueous solution which was separated into an oily layer and an aqueous layer, the latter of which was extracted with benzene. The benzene extract was distilled under reduced pressure to obtain N-methyl-N-benzyl-n-dodecylamine, b.p. 146 ~ 149° C./0.4 mmHg.

Workup

  1. temperatureheated at 90°~100° C
  2. waitAfter several minutes
  3. temperaturethe mixture was again refluxed at 90°~100° C. for 8 hours
  4. additionwas added to the cooled reaction mixture, which
  5. customcondensed to dryness under reduced pressure
  6. customwas separated into an oily layer
  7. extractionan aqueous layer, the latter of which was extracted with benzene
  8. extractionThe benzene extract
  9. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-fb96d34ecf6347bb8636de81573ad3ee
Source dataset
uspto-grants-1979_05
Patent number
US04155872

Reaction notes

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