تفاعل #94116

معادلة التفاعل

benzylamine

3-bromo-1-indanone

→

title product

3-Benzylamino-1-indanol

المذيبات

ether

ether

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONadd
2. 2
   أخرىStore the reaction under nitrogen at -10° C. for one day
3. 3
   ترشيحQuickly filter the cold solution
4. 4
   workup.ADDITIONadd it cold to a stirring solution of one molar borane in tetrahydrofuran (60 ml.) below 0° C.
5. 5
   workup.STIRRINGStir the solution for 18 hours at room temperature
6. 6
   workup.ADDITIONCarefully add a solution of water (3.24 ml.) in tetrahydrofuran (20 ml.) dropwise
7. 7
   workup.STIRRINGof 5M isopropanolic --HCl, and continue stirring overnight
8. 8
   أخرىStore the reaction at -10° C. overnight
9. 9
   ترشيحfilter the precipitate
10. 10
    ترشيحthrough filter-aid
11. 11
    استخلاصExtract the dry solid mixture with methanol-methylene chloride
12. 12
    ترشيحfilter
13. 13
    أخرىevaporate the solvents in vacuo
14. 14
    أخرىTriturate the resulting solid with cold ethyl acetate
15. 15
    ترشيحfilter
16. 16
    أخرىdry
17. 17
    أخرىto obtain 2.36 g

الإجراء التجريبي

Cool a solution of benzylamine (3.22 g.) in dry ether (25 ml.) to below 0° C. With stirring under nitrogen add a cooled (below 0° C.) solution of 3-bromo-1-indanone (3.17 g.) in ether (25 ml.) dropwise over 1.5 hours. Store the reaction under nitrogen at -10° C. for one day. Quickly filter the cold solution and add it cold to a stirring solution of one molar borane in tetrahydrofuran (60 ml.) below 0° C. and under nitrogen. Stir the solution for 18 hours at room temperature. Carefully add a solution of water (3.24 ml.) in tetrahydrofuran (20 ml.) dropwise, followed by 8.0 ml. of 5M isopropanolic --HCl, and continue stirring overnight. Store the reaction at -10° C. overnight, then filter the precipitate through filter-aid. Extract the dry solid mixture with methanol-methylene chloride, filter and evaporate the solvents in vacuo. Triturate the resulting solid with cold ethyl acetate, filter and dry to obtain 2.36 g. of the title product as the hydrochloride salt, m.p. 233-235°. λmaxKBr 3.0 μ (OH).

المصدر