تفاعل #51614

معادلة التفاعل

N″-cyano-N-[1-[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-4-piperidinyl]-N′-(2,2-dimethoxyethyl)guanidine

HCl

Na2CO3

→

[1-[1-[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-4-piperidinyl]-1H-imidazol-2-yl]cyanamide

(±)-[1-[1-[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-4-piperidinyl]-1H-imidazol-2-yl]urea

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةrefluxed for 100 minutes
2. 2
   أخرىto obtain
3. 3
   أخرىa clear separation
4. 4
   أخرىThe organic layer was separated
5. 5
   workup.ADDITIONDCM was added
6. 6
   غسيلthe whole was washed with water
7. 7
   أخرىdried
8. 8
   ترشيحfiltered
9. 9
   أخرىthe solvent was evaporated
10. 10
    أخرىThe residue was separated
11. 11
    أخرىpurified by column chromatography over silica gel (separation first compound: eluent: CH2Cl2/CH3OH 95/5; separation second compound: CH2Cl2/(CH3OH/NH3) 90/10)
12. 12
    أخرىThe two pure fraction groups were collected
13. 13
    أخرىtheir solvent was evaporated
14. 14
    أخرىEach residue was crystallized from ACN
15. 15
    ترشيحEach precipitate was filtered off
16. 16
    أخرىdried

الإجراء التجريبي

A mixture of N″-cyano-N-[1-[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-4-piperidinyl]-N′-(2,2-dimethoxyethyl)guanidine (0.0153 mol) and HCl (0.5 N, 46 ml) in THF (160 ml) was stirred and refluxed for 100 minutes. Ice-water was added. Na2CO3 was added portionwise to obtain a clear separation. The organic layer was separated, DCM was added, the whole was washed with water, dried, filtered and the solvent was evaporated. The residue was separated and purified by column chromatography over silica gel (separation first compound: eluent: CH2Cl2/CH3OH 95/5; separation second compound: CH2Cl2/(CH3OH/NH3) 90/10). The two pure fraction groups were collected and their solvent was evaporated. Each residue was crystallized from ACN. Each precipitate was filtered off and dried, yielding 1.75 g [1-[1-[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-4-piperidinyl]-1H-imidazol-2-yl]cyanamide (compound 59) and 0.48 g (±)-[1-[1-[(3,4-dihydro-2H-1-benzopyran-2-yl)methyl]-4-piperidinyl]-1H-imidazol-2-yl]urea (compound 66).

المصدر