i think it's safe to assume that you have the "mappedBy" attribute set for the 
User side of the relationship, right?

the mappedBy attribute basically says which side of the relationship is 
responsible for maintaining the DB foreign key link. so, you could try this in 
your existing code:

  | User[] users = portal.getUsers();
  | for(User user : users)
  | {
  |   user.setPortal(null); //or user.removePortal(), whatever your method is
  | }
  | 
  | em.remove(portal);
  | 


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