1 Enoch 14:5
4 I wrote out your petition, and in my vision it appeared thus, that your petition will not be granted unto you ⌈⌈throughout all the days of eternity, and that judgement has been finally passed upon you: yea (your petition) will not be granted unto you⌉⌉. 5 And from henceforth you shall not ascend into heaven unto all eternity, and ⌈in bonds⌉ of the earth the decree has gone forth to bind you for all the days of the world. 6 And (that) previously you shall have seen the destruction of your beloved sons and ye shall have no pleasure in them, but they shall fall before you by the sword.
1 Peter 3:19
18 Because Christ also suffered once for sins, the just for the unjust, to bring you to God, by being put to death in the flesh but by being made alive in the spirit. 19 In it he went and preached to the spirits in prison, 20 after they were disobedient long ago when God patiently waited in the days of Noah as an ark was being constructed. In the ark a few, that is eight souls, were delivered through water.
Notes and References
"... It is important to note that, in both 1 Enoch and 2 Enoch, the fallen angels are described expressly, as being “in prison,” or in equivalent terms. In 1 Enoch, they are condemned by God to prison as they await their final judgment (1 Enoch 14:5; compare 18:14). The reference to the spirits being imprisoned is decisive. Any literate Second Temple period Jewish reader of 1 Peter 3:19 would have understood that Peter was referring to fallen nonhuman spirits, the Watchers who sinned before the Flood (Genesis 6:2) ..."
Heiser, Michael S. Reversing Hermon: Enoch, the Watchers & the Forgotten Mission of Jesus Christ (pp. 129-130) Defender Publishing, 2017