Nitrogen → Butylamine

HRID 482152Notes

Reaction equation

HRID 482152 reaction equation
CO[C:3](=[O:25])[C@H:4]([CH2:19][CH2:20][C:21]([O:23]C)=[O:22])[NH:5][C:6](=[O:18])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C[CH:27]1[CH2:32][CH2:31][CH2:30]CC1(C)C.CC1(CC)CCCCC1.C(C1(CC)CCCCC1)C.N#N.[CH2:56]([NH2:60])[CH2:57][CH2:58][CH3:59]>CO.C1CCCCC1>[CH2:56]([N:60]([CH2:30][CH2:31][CH2:32][CH3:27])[C:3](=[O:25])[C@H:4]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[NH:5][C:6](=[O:18])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:57][CH2:58][CH3:59].[CH2:4]([NH2:5])[CH2:19][CH2:20][CH3:21]

Participants

10

Reactant 6

HCID 947NitrogenHCID 8007ButylamineHCID 353631,1,2-TrimethylcyclohexaneHCID 354111-Methyl-1-ethylcyclohexaneHCID 10948302HCID 10948302, compoundHCID 126449441,1-Diethylcyclohexane

Product 2

HCID 8007ButylamineHCID 12049931lauroyl glutamic dibutylamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8078CyclohexaneSolvent

Procedure

In a 1 I Quickfit flask with a glass-jacketed thermosensor, gas inlet, stainless steel anchor stirrer and heatable (67°-70° C.) pre-column with an attached Claisen bridge and subsequent cold trap, 110 g of N-lauroyl-L-glutamic acid dimethyl ester (LGA-DME) and 100 g of a mixture of cyclohexane derivatives (trimethylcyclohexane, methylethylcyclohexane and diethylcyclohexane in an approximate ratio of 45:25:10) are initially introduced under a gentle stream of N2. 110 g of n-butylamine are metered in over a period of 30 minutes and the mixture is heated under reflux. During the reaction, portions of the methanol liberated during the amidation are separated off, with a little n-butylamine, via the temperature-controlled pre-column. After refluxing for about 8 hours, monitoring by TLC indicates quantitative conversion. The excess n-butylamine is distilled off, first under normal pressure and then in vacuo, and the product is precipitated by addition of acetone. The precipitate formed is filtered off with suction, washed with acetone, dried and comminuted. The target product N-lauroyl-L-glutamic acid di-n-butylamide is obtained in a good yield of about 80% and in excellent purity (LGB 99% (HPLC), nBuNH2 50 ppm (GC), other impurities<1%) in the form of a colorless powder of melting point 150°-152° C.

Workup

  1. customare metered in over a period of 30 minutes
  2. temperaturethe mixture is heated
  3. temperatureunder reflux
  4. customare separated off, with a little n-butylamine, via the temperature-controlled pre-column
  5. temperatureAfter refluxing for about 8 hours
  6. distillationThe excess n-butylamine is distilled off, first under normal pressure
  7. customin vacuo, and the product is precipitated by addition of acetone
  8. customThe precipitate formed
  9. filtrationis filtered off with suction
  10. washwashed with acetone
  11. customdried
  12. customcomminuted

Sources & evidence

ORD record
ord-a1a2a45c9a7a424283ab7deba2c6d8f2
Source dataset
uspto-grants-1998_08
Patent number
US05792880

Reaction notes

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