Tert-Butylamine → HCID 11695501, compound

HRID 1732051Notes

Reaction equation

HRID 1732051 reaction equation
[CH:1]12[O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6]2.[C:8]([NH2:12])([CH3:11])([CH3:10])[CH3:9]>C1(C)C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[OH:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[NH:12][C:8]([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 9246Cyclohexene oxide

Product 1

HCID 11695501HCID 11695501, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
120 °C

Procedure

A mixture of cyclohexene oxide (19.6 g), t-butyl amine (37.1 g), zinc chloride (2.5 g), and 50 ml of toluene were sealed under an inert atmosphere in a Diels-Alder flask. The contents were stirred and heated in a sand bath at 120° C. for 23 hours. After cooling the slurry was diluted with 100 ml of toluene, washed with dilute ammonium hydroxide solution (3×250 ml) and water (300 ml), dried (Na2SO4), filtered, and the solvents were removed under reduced pressure to give 31.6 g of N-2-hydroxycyclohexyl-N-t-butylamine as an off-white, waxy solid, m.p. 42°-44° C.

Workup

  1. customwere sealed under an inert atmosphere in a Diels-Alder flask
  2. temperatureAfter cooling the slurry
  3. washwashed with dilute ammonium hydroxide solution (3×250 ml) and water (300 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-99fbf91923e040d7b8abdf67cd57d023
Source dataset
uspto-grants-1986_11
Patent number
US04624980

Reaction notes

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