Starting with the infinite series representation
$$\csc(x)=\frac 1 x+\sum_{p=1}^\infty (-1)^p\,\frac{ 2^{2 p}\, B_{2 p}\left(\frac{1}{2}\right) }{(2 p)!} x^{2p-1}$$ let $x=\frac k n \pi$ to make
$$\csc \left(\frac{\pi k}{n}\right)=\frac{n}{\pi k}+\sum_{p=1}^\infty (-1)^p\,\frac{2^{2p}\,\pi ^{2 p-1} B_{2 p}\left(\frac{1}{2}\right)
}{n^{2p-1}(2 p)!}\,k^{2 p-1}$$ The first summation does not make any problem
$$\sum_{k=1}^{n-1}\frac{n}{\pi k}=\frac{n}{\pi } H_{n-1}$$
$$\sum_{k=1}^{n-1}\csc \left(\frac{\pi k}{n}\right)=\frac{n}{\pi } H_{n-1}+S_n$$ These $S_n$ seem to be complicated and I did not find any reasonable approximation.
At this point, I give up hoping that some users could continue.
What we can notice is that the sum is "not very far" from the integral
$$I_n=\int_{1}^{n-1} \csc \left(\frac{\pi k}{n}\right)\,dk=\frac {2}\pi\,n\,\log \Big[\cot \left(\frac{\pi }{2 n}\right)\Big]$$ the asymptotics of which being
$$I_n=\frac{2 n \log \left(\frac{2 n}{\pi }\right)}{\pi }-\frac{\pi }{6 n}+O\left(\frac{1}{n^3}\right)$$ So, to provide some results, for $1 \leq n \leq 500$, I pefromed some data anlysis.
What I found is that a model such
$$\sum_{k=1}^{n-1}\csc \left(\frac{\pi k}{n}\right)=\frac{2 n \log \left(\frac{2 n}{\pi }\right)}{\pi }+ an$$ could be quite good.
Adjusted, $a=0.3674659$ $(\sigma_a=7.33\times 10^{-7})$ and making it rational, the proposed model is
$$\sum_{k=1}^{n-1}\csc \left(\frac{\pi k}{n}\right)\sim\frac{2 n \log \left(\frac{2 n}{\pi }\right)}{\pi }+ \frac{445}{1211}n+ O\left(\frac{1}{n}\right)$$
Just a few results
$$\left(
\begin{array}{ccc}
n & \text{approximation} & \text{exact} \\
50 & 128.5224811 & 128.5208358 \\
100 & 301.1720822 & 301.1714095 \\
150 & 490.4771890 & 490.4769072 \\
200 & 690.5984044 & 690.5983681 \\
250 & 898.7624047 & 898.7625556 \\
300 & 1113.335738 & 1113.336047 \\
350 & 1333.239074 & 1333.239525 \\
400 & 1557.705289 & 1557.705871 \\
450 & 1786.160804 & 1786.161510 \\
500 & 2018.160409 & 2018.161235
\end{array}
\right)$$