N,N-Dimethylcyclohexylamine → HCID 60714666, compound

HRID 1732050Notes

Reaction equation

HRID 1732050 reaction equation
[CH:1]12[O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.[C:8]([NH2:16])([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:10])[CH3:9].CN(C1CCCCC1)C>C(Cl)Cl.[Cl-].[Zn+2].[Cl-]>[C:8]([NH:16][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][CH:1]1[OH:7])([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:10])[CH3:9]

Participants

6

Reactant 3

HCID 7415N,N-DimethylcyclohexylamineHCID 9246Cyclohexene oxideHCID 61017tert-Octylamine

Product 1

HCID 60714666HCID 60714666, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

In a 1000 cc three neck flask was charged 86.6 gms (0.88 moles) of cyclohexene oxide, 114.0 gms (0.88 moles) of t-octyl amine, 5 grams of zinc chloride, and 2.2 gms of polycat-8 (Abbot Laboratories). The mixture was then heated at 95°-100° C. for about 10 hours. The crude mixture was stripped of low boilers and then was dissolved in methylene chloride and washed with ammonium hydroxide solution. The methylene chloride solution was dried over magnesium sulfate, filtered and stripped to give a liquid. The product was distilled at 121° C. (0.3 mmHg) to give a colorless liquid. A GLC analysis of the distilled product showed it to be 98.6% purity.

Workup

  1. temperatureThe mixture was then heated at 95°-100° C. for about 10 hours
  2. washwashed with ammonium hydroxide solution
  3. dry with materialThe methylene chloride solution was dried over magnesium sulfate
  4. filtrationfiltered
  5. customto give a liquid
  6. distillationThe product was distilled at 121° C. (0.3 mmHg)
  7. customto give a colorless liquid

Sources & evidence

ORD record
ord-61febe9ff46941bdaac4cc8c5f7b0763
Source dataset
uspto-grants-1986_11
Patent number
US04624980

Reaction notes

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