반응 #61980

반응 방정식

sodium bicarbonate

product

4-(3-Chloro-propoxy)-benzaldehyde

1,2,3,4-tetrahydro-isoquinoline

sodium triacetoxyborohydride

piperidine

sodium carbonate

potassium iodide

→

title compound

2-[4-(3-Piperidin-1-yl-propoxy)-benzyl]-1,2,3,4-tetrahydro-isoquinoline

용매

n-butanol

water

DCE

acetic acid

반응 조건

후처리

1. 1
   추출The resulting mixture was extracted with DCM (3×10 mL)
2. 2
   건조The combined organic phases were dried (magnesium sulfate)
3. 3
   기타evaporated
4. 4
   기타giving a material which
5. 5
   workup.WAITAfter 16 h
6. 6
   온도the reaction was cooled to RT
7. 7
   추출extracted with DCM (3×20 mL)
8. 8
   건조The combined organic phases were dried (magnesium sulfate)
9. 9
   기타evaporated
10. 10
    workup.ADDITIONThe residue was treated with ether (20 mL)
11. 11
    여과filtered
12. 12
    workup.ADDITIONThe filtrate was treated with hydrogen chloride (2.5 mL of a 2 M solution in ether)
13. 13
    기타evaporated
14. 14
    건조The residue was dried in vacuo, and ether
15. 15
    workup.ADDITIONwas added
16. 16
    기타to form
17. 17
    여과Filtration

실험 절차

A solution of the product of Example 11 (1.0 g), 1,2,3,4-tetrahydro-isoquinoline (0.0.69 mL), and acetic acid (0.29 mL) in DCE (10 mL) was treated with sodium triacetoxyborohydride (1.5 g). After 16 h, saturated aqueous sodium bicarbonate was added. The resulting mixture was extracted with DCM (3×10 mL). The combined organic phases were dried (magnesium sulfate) and evaporated, giving a material which was dissolved in n-butanol (20 mL), treated with piperidine (0.65 mL), sodium carbonate (800 mg), and potassium iodide (42 mg), and heated to 105° C. After 16 h, the reaction was cooled to RT, treated with water (10 mL), and extracted with DCM (3×20 mL). The combined organic phases were dried (magnesium sulfate) and evaporated. The residue was treated with ether (20 mL), and filtered. The filtrate was treated with hydrogen chloride (2.5 mL of a 2 M solution in ether) followed by methanol (3 mL). The resulting solution was stirred for 1 h, and evaporated. The residue was dried in vacuo, and ether was added, followed by enough methanol to cause a precipitate to form. Filtration gave the title compound as an amorphous pink powder (0.86 g). 1H NMR (400 MHz, CDCl3): 7.27 (d, J=8.6 Hz, 2H), 7.13-7.05 (m, 4H), 6.99-6.96 (m, 1H), 6.89-6.83 (m, 2H), 4.00 (t, J=6.3 Hz, 2H), 3.60 (s, 4H), 2.89 (t, J=5.7 Hz, 2H), 2.72 (t, J=5.8 Hz, 2H), 2.53-2.37 (m, 6H), 2.03-1.95 (m, 2H), 1.64-1.57 (m, 4H), 1.49-1.40 (m, 2H).

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