تفاعل #710494

معادلة التفاعل

1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-one

ammonium acetate

sodium cyanoborohydride

→

desired product

المردود 33.2%

3-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-amine

المردود 33.2%

المذيبات

methanol

ظروف التفاعل

المعالجة

1. 1
   ترشيحAfter filtration
2. 2
   تركيزThe reaction mixture was concentrated to dryness and 30 mL of ethyl acetate
3. 3
   workup.ADDITIONwere added
4. 4
   غسيلThe organic phase was washed with an aqueous solution of 1 N sodium hydroxide, brine and water
5. 5
   تجفيفdried over magnesium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated to dryness
8. 8
   workup.DISSOLUTIONThe crude material was dissolved in 15 mL of 1 N hydrochloric acid
9. 9
   استخلاصextracted with 15 mL of ethyl acetate
10. 10
    workup.ADDITIONAn aqueous solution of 1 N sodium hydroxide was added to the aqueous phase, which
11. 11
    استخلاصwas subsequently extracted twice with 15 mL of ethyl acetate
12. 12
    تجفيفThe organic phase was dried over magnesium sulfate
13. 13
    ترشيحfiltered
14. 14
    تركيزconcentrated to dryness

الإجراء التجريبي

0.64 g of 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-one (Int-12) (0.0025 mol) were diluted in 5 mL of methanol. 7.0 g of molecular sieves 3 Å, 1.90 g (0.025 mol) of ammonium acetate and 0.39 g (0.0052 mol) of sodium cyanoborohydride were added. The reaction medium was stirred overnight at room temperature. After filtration, the pH was adjusted to 9 with an aqueous solution of 1 N sodium hydroxide. The reaction mixture was concentrated to dryness and 30 mL of ethyl acetate were added. The organic phase was washed with an aqueous solution of 1 N sodium hydroxide, brine and water; dried over magnesium sulfate, filtered and concentrated to dryness. The crude material was dissolved in 15 mL of 1 N hydrochloric acid and extracted with 15 mL of ethyl acetate. An aqueous solution of 1 N sodium hydroxide was added to the aqueous phase, which was subsequently extracted twice with 15 mL of ethyl acetate. The organic phase was dried over magnesium sulfate, filtered and concentrated to dryness. 0.21 g (32%) of desired product 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]butan-2-amine (IIa-16) were obtained, [M+1]=253.

المصدر