[Mr. Jack]

I have been studying alternate ways to chlorinate tertiary amino 2-ols (without using the EXPENSIVE and regulated, thionyl chloride).  During my "research" I discovered that secondary alcohols could be chlorinated using Lucas' Reagent (HCl + ZnCl₂).  However, someone on another forum told me that it's possible that ammonia might act as a ligand and form complexes with various metal ions and might complicate the resulting aminochloroalkane's isolation.  Does anyone have experience with this and, if so, do you know if this is the case?

Since amino groups form salts with acids, I am, of course, speaking of chlorinating the HCl salt of the amino alcohol.  Also, let's assume the amino group is protected with 2 alkyl groups.

So....

R     H   H  H
  \    |    |   |
  N--C--C--C--H
  /    |   |    |
R     H OH H 

is the molecule that needs to be chlorinated.

Thanks, in advance, for your help.

[Kryolith]

A zinc(II)-salt an ammonia can react to Zn(OH)₂ that precipitates. With an excess of NH₃ it dissolves under formation of [Zn(NH₃)₄]²⁺. I can't imagine such processes take place under acidic conditions.
If you don't want to use SOCl₂, try a combination of CCl₄ (possibly carcinogenic) and PPh₃ (appel reagent).