N-Methylbutylamine → HCID 58516527, compound

HRID 1254180Notes

Reaction equation

HRID 1254180 reaction equation
O=P(Cl)(Cl)Cl.[CH:6]1([N:12]([CH3:22])[C:13]([NH:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=O)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[CH2:23]([NH:27][CH3:28])[CH2:24][CH2:25][CH3:26].[OH-].[Na+]>C1(C)C=CC=CC=1.O>[CH2:23]([N:27]([CH3:28])[C:13]([N:12]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[CH3:22])=[N:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[CH2:24][CH2:25][CH3:26]

Participants

7

Reactant 4

HCID 8068N-MethylbutylamineHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 8536641,3-dicyclohexyl-1-methylurea

Product 1

HCID 58516527HCID 58516527, compoundYield 38,821.301%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

18.38 g of cyclohexyl isocyanate (0.147 mol) are added, dropwise, to a solution of 19.12 g of N-methyl-N-cyclohexylamine (0.169 mol) in 160 ml of hexane, and then the cloudy mixture is refluxed for 2 h and then evaporated to dryness, to give 35 g of crude N,N′-dicyclohexyl-N-methylurea. 12 g of POCl3 (78 mmol) are added, over the course of 1 h, to a suspension of 17 g of said crude N,N′-dicyclohexyl-N-methylurea (71.33 mmol) in 65 ml of dry toluene, and then, after a few hours at 20° C., 15.5 g of N-butyl-N-methylamine (0.178 mmol) are added over the course of 2 h, and then, after a further 2 h at 20° C., 50 ml of water are added. 49 g of 35% sodium hydroxide are then added while cooling, and then the two-phase medium is extracted with diisopropyl ether. After drying and evaporation to dryness, the oil obtained, 26.5 g, is distilled at 180° C. under 1 mbar, to give 21.25 g of the expected guanidine (yield 97%).

Workup

  1. waitafter a few hours at 20° C.
  2. temperaturewhile cooling
  3. extractionthe two-phase medium is extracted with diisopropyl ether
  4. customAfter drying
  5. customevaporation to dryness
  6. customthe oil obtained
  7. distillation26.5 g, is distilled at 180° C. under 1 mbar

Sources & evidence

ORD record
ord-f123e79eab6244038644f531fdc46301
Source dataset
uspto-grants-2013_06
Patent number
US08455562B2

Reaction notes

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