Daniel 11:21-25
Daniel 11:21
And in his estate shall stand up a vile person, to whom they shall not give the honour of the kingdom: but he shall come in peaceably, and obtain the kingdom by flatteries.
Demetrius the son of Seleucus IV should have been the rightful heir to the throne but at the time he was being held hostage in Rome.  There was also another child left by Seleucus IV and that was Seleucus Ceraunus.  Enter the king’s brother Antiochus IV Epiphanes who usurped the throne and claimed he was gaining the throne for his nephew Demetrius.  He had flattered King Eumenea of Pergamem and he also received a helping hand from Rome.  His vileness will show up in what he will do to the Jews, Jerusalem, and the Temple.
Daniel 11:22
And with the arms of a flood shall they be overflown from before him, and shall be broken; yea, also the prince of the covenant.
Antiochus IV was in Rome at the time of the death of Seleucus IV and quickly came back and did away with the heirs and also Heliodorus.  Antiochus then took the throne and broke the armies of Egypt.  The “prince of the covenant” in this case was the High priest Onias III who was killed in 171 B.C.  His own brother Menelaus was involved in his death.
Daniel 11:23
And after the league made with him he shall work deceitfully: for he shall come up, and shall become strong with a small people.
The league in view here was the promised dowry of Cleopatra I.  Her sons, Ptolemy VI Philometor and Ptolemy VII Physcom had demanded that Syria and Palestine be that dowry.  Instead, Antiochus had acted deceitfully and made war with Egypt.  Much of his territory was stripped from him so that he was a small nation or people. 
Daniel 11:24
He shall enter peaceably even upon the fattest places of the province; and he shall do that which his fathers have not done, nor his fathers' fathers; he shall scatter among them the prey, and spoil, and riches: yea, and he shall forecast his devices against the strong holds, even for a time.
Antiochus IV had defeated the Egyptians and as a result had crowned himself king of Upper Egypt at Memphis.  This was something that none of his predecessors had ever done.  Then he took the spoils from the wealthy areas and distributed it to the poor people.  He also weakened the fortresses in Syria to insure that he had no strong opposition in his own country of Syria.  This move proved successful for the balance of his reign of twelve years.
Daniel 11:25
And he shall stir up his power and his courage against the king of the south with a great army; and the king of the south shall be stirred up to battle with a very great and mighty army; but he shall not stand: for they shall forecast devices against him.
Antiochus IV Epiphanes had at least two campaigns against lower Egypt, against the king of the south Ptolemy VI Philometor.  He defeated him at Pelusium in 170 B.C.  He also made an unsuccessful attempt to attack Ptolemy VII in lower Egypt in Alexandria.  There was treason in the ranks of the army of Ptolemy VI and that is why he lost the battle at Pelusium.