Cyclohexylamine → HCID 23347815, compound

HRID 1855722Notes

Reaction equation

HRID 1855722 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7](=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH:14]1([NH2:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>CCOCC.CCCCC.[Ti](Cl)(Cl)(Cl)Cl>[CH:14]1([N:20]=[C:7]([C:3]2[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 2

HCID 7965CyclohexylamineHCID 89094Ethyl 1-methyl-alpha-oxo-1H-pyrrole-2-acetate

Product 1

HCID 23347815HCID 23347815, compoundYield 15%

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 3283Diethyl EtherSolventHCID 8003PentaneSolvent

Procedure

To a solution of 25 g ethyl 1-methylpyrrole-2-glyoxylate and 44.5 g cyclohexylamine in 700 ml ether under nitrogen at 0° C. is added 8.8 ml of titanium tetrachloride in 80 ml pentane. After stirring at room temperature overnight, the precipitate is removed by filtration. The filtrate is evaporated and the resulting oil distilled. The fraction collected at 111°-117° C. (5 millitorr) is crystallized from hexane to afford a 15% yield of ethyl α-cyclohexylimino-1-methylpyrrole-2-acetate, m.p. 35°-36° C.

Workup

  1. customthe precipitate is removed by filtration
  2. customThe filtrate is evaporated
  3. distillationthe resulting oil distilled
  4. customThe fraction collected at 111°-117° C. (5 millitorr)
  5. customis crystallized from hexane

Sources & evidence

ORD record
ord-dc0335ebc12a49229b0f612b77124da1
Source dataset
uspto-grants-1980_08
Patent number
US04216150

Reaction notes

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