First of all we check the behaviour of the integrand for small $x$. The ratio $\sin(x)/x$ is then slightly smaller than one, so we can indeed take the arcsin and obtain the limit value of $\pi /2$. Hence there is no problem for $x$ around zero.
Next we check the behaviour for large values of $x$. It is convenient to rewrite the formula for the integrand $f = \arcsin(\sin(x)/x))$ as $\sin(f) = \sin(x)/x$. We consider an interval of width $2\pi$ around the central value $x_0 = (2N + 1/2)\pi$, with $N$ large. Then the RHS is given by:
$$RHS = \sin((2N+1/2)\pi +\delta)/((2N+1/2)\pi+\delta) = \cos(\delta)/(x_0+\delta)$$
where $\delta$ is defined as $\delta = x-x_0$. Since $\delta$ is small compared to $x_0$ we can expand the denominator up to third order in $x_0$:
$$RHS = \cos(\delta)(1/x_0 - \delta/x_0^2 + \delta^2/x_{0}^{3})$$
The LHS can be expanded for small values of $f$ as $LHS = \sin(f) = f - f^3 /6$. Combining these results we obtain, correct up to third order in $1/x_0$:
$$f = \cos(\delta)(1/x_0 - \delta/x_0^2 + \delta^2/x_{0}^{3}) + \cos(\delta)^3/6x_0^3$$
We now integrate over the interval $(-\pi, \pi)$. We see that the first order term vanishes (integrating a cosine over $2\pi$) and also the second order term (antisymmetric function). Hence the integral yields a contribution of third order and higher in $x_0$. Contributions from successive intervals can therefore be summed without difficulty and the result converges. Therefore the integral as a whole converges.