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In the chapter 3 of Nicomachean Ethics' book II, Aristotle says:

Again, if the virtues are concerned with actions and passions, and every passion and every action is accompanied by pleasure and pain, for this reason also virtue will be concerned with pleasures and pains. [...]

I know Theophrastus, a pupil of Aristotle, is "credited with investigations into hypothetical syllogisms" and that the phrase might not fit in the formula perfectly, but I'd like to know if a reasoning like this could be considered a proto-hypothetical-syllogism or even a sort of Theophrastus' influece somehow.

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From that passage alone, no. Merely to say that actions and passions are accompanied by pleasures and pains is merely to identify a correlation.

However, if we look at BK I of the Nicomachean Ethics, then we have two details that at first glance sound like a hypothetical syllogism:

  1. The argument from the first part about intermediate and final ends and that the end we are all seeking is eudaimonia ("flourishing" or "happiness")
  2. The argument from the second half that we achieve eudaimonia by following our ergon ("function")

These two together give us: If you want to eudaimonia, then you should follow your ergon.

But after that, several things are going to raise questions as to whether this is anything like what Kant calls a hypothetical syllogism.

In the Groundwork BK II, Kant identifies two types of hypothetical syllogisms:

  • Rules of skill -- if you want to swim, move your arms and legs in the right way.
  • Counsels of prudence -- to be happy, do X.

and contrasts this with the categorical imperative which is a command which has no qualifier or contigencies and apply to rational agents qua rational agents.


Unfortunately, this does not settle the matter of whether what Aristotle is describing can be properly understood as a "hypothetical imperative" for two reasons.

First, in later works, Kant identifies the highest good as unifying the goals of pure practical reason and empirical practical, which are virtue and happiness respectively (see Bader). This stands in contrast with the "supreme good" which is just virtue. This account spans Critique of Pure Practical Reason, Metaphysics of Morals, and Religion within the Bounds of Reason Alone on the side of critical philosophy and bridges with Kant's Anthropology (which is from the side of empirical reason).

This arrangement differs quite a bit from what people learn when they read the Groundwork. This leads to three possibilities: (1) Kant changed his mind, (2) Kant does not think the pursuit of happiness is always a hypothetical syllogism, or (3) it is wrong to construe counsels of prudence as not moral in Kant's philosophy.

Second, is Aristotle's account hypothetical as intended by Aristotle. Yes, it is saying if you want to be happy, then follow your function. But this same sort of contingency exists in Kant: if you a rational being, then act in accordance with the categorical imperative. Stated another way, neither is suggesting the command is contingent on what you want -- both are stating that it is contingent on what you are.

References

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