High range works with a sliding gear. Either the gear is broken, or . . . the shifter and fork is not working to push it into place. Can easily happen just from a broken roll or groove pin. Does the shifter feel like it's going where it ought to?
Regardless, you're going to have to pull the trans top-cover off to see what the culprit is.
Some 3414s are setup just like B-275 and B-414 farm tractors and others are quite different. Can have a gear reverser, a torque converter drive, etc. If you just have a clutch driven machine with a hi-low gear range, I suspect you have shift linkage problems.
Hi-low range shift handle attaches to the crossshaft with a 1/4" X 1 1/4" long groove pin.
That hi-low crossshaft attaches to a hi-low shift cam via a 3/16" X 1 1/8" long groove pin.
The hi-low shift cam attaches to the hi-low shift rail/fork with an ear that sits in a groove in the shaft. The ear can break , but I doubt that's your problem.
The hi-low shift rail/fork has a fork that sits in the gear-collar (gear the moves).
With all of the above, I'd suspect a broken groove pin first. If so, a cheap easy fix.
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