Water → 2-(Triphenylmethoxy)ethan-1-amine

HRID 80300Notes

Reaction equation

HRID 80300 reaction equation
[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)Cl)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH2:22]([CH2:24][NH2:25])[OH:23].O>N1C=CC=CC=1>[C:1]1([C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:23][CH2:22][CH2:24][NH2:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6456Trityl chlorideHCID 74819Ethanolamine Hydrochloride

Product 1

HCID 138305502-(Triphenylmethoxy)ethan-1-amineYield 28.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Triphenylchloromethane (1.00 g, 3.58 mmol) (Wako Pure Chemical Industries, Ltd.) and ethanolamine hydrochloride (1.00 g, 10.3 mmol) (Wako Pure Chemical Industries, Ltd.) were dissolved in pyridine (4 mL), and the solution was stirred at room temperature for 3 days. Water (200 mL) was poured into the reaction solution, and the precipitates were suction-filtered. The solid matters were suspended in diethyl ether, and 3 (N) hydrochloric acid (Wako Pure Chemical Industries, Ltd.) was added thereto, followed by stirring at room temperature for 15 minutes. The insoluble matters were suction-filtered. The insoluble matters were dissolved in a mixed solution of ethyl acetate (Wako Pure Chemical Industries, Ltd.) and a saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.), and the mixture was shaken, followed by the separation of the organic layer. The organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and then suction-filtered and concentrated under reduced pressure, to thereby obtain the title compound (0.31 g, 28% yield).

Workup

  1. filtrationthe precipitates were suction-filtered
  2. addition3 (N) hydrochloric acid (Wako Pure Chemical Industries, Ltd.) was added
  3. stirringby stirring at room temperature for 15 minutes
  4. filtrationThe insoluble matters were suction-filtered
  5. dissolutionThe insoluble matters were dissolved in a mixed solution of ethyl acetate (Wako Pure Chemical Industries, Ltd.)
  6. stirringa saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.), and the mixture was shaken
  7. customfollowed by the separation of the organic layer
  8. dry with materialThe organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
  9. filtrationsuction-filtered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ecd98778443d418ba5795531736883e0
Source dataset
uspto-grants-2014_09
Patent number
US08846012B2

Reaction notes

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