How to say his heart bled for his lost friend. in Japanese

1)亡き亡き(naki) (adj-pn,n) the late/the deceased友(tomo) (n) friend/companion/comrade/palを(wo) (prt) indicates direct object of action/indicates subject of causative expression/indicates an area traversed/indicates time over which action takes place/indicates point of departure or separation of action/indicates object of desire, like, hate,思い思い(omoi) (n) thought/imagination/mind/heart/desire/wish/hope/expectation/love/affection/feelings/emotion/sentiment/experience彼(kare) (ok) that , or something understood without naming it directly)/that person/over there/hey/eh?/thatは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sigh悲(hi) (n) karunaし(shi) (num) 10^24/septillion/quadrillionんだんだ(nda) (exp) the expectation is that .../the reason is that .../the fact is that .../it is that ...。(。) Japanese period "."    
naki tomo wo omoi kareha kanashi nda 。
Grammer form日常会話 (Casual form)Casual form (nichijoukaiwa)
everyday casual language, commonly used between friends and family.
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