ChemicalBook CAS DataBase List 1-Pentanol, 5-(methylamino)-

1-Pentanol, 5-(methylamino)- synthesis

10synthesis methods

Product Name:1-Pentanol, 5-(methylamino)-
CAS Number:2751-70-4
Molecular formula:C6H15NO
Molecular Weight:117.1894

95732-46-0
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2751-70-4
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Yield:2751-70-4 97 %

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 0 - 80;

Steps:

6.1.3.a

Next, a flame-dried 250 mL round-bottom flaks was charged with 694 mg LiAlhU (18.3 mmol, 1.2 eq.) and 22 mL dry THF. The mixture was cooled to 0° C. 1 eq. N-(5-hydroxypentyl) formamide (2 g, 15.2 mmol) from the previous reaction was dissolved in 5 mL dry THF and added drop-wise under strong stirring and continuous cooling. A gray precipitate formed rapidly. After complete addition of the reagents, the mixture was heated to 80° C and stirred under reflux conditions for 2 h. The reaction was stopped by the addition of 2 mL 15% NaOH and some drops of water. It was dried over MgSCU the precipitated was removed by filtration and washed extensively with THF. 1 .8 g crude 5(-methylamino)pentan-1-ol was collected as a colourless oil. A small proportion was purified over 12 g S1O2 with 6 to 20% MeOH in DCM over 8 CV. Residual silica gel was removed by filtration over a short plug of Celite and the desired compound was afforded in 97% yield. ¹H NMR (400 MHz, MeOD): δ 3.47 (t, 3H), 3.27 (s, 3H), 3.16 (q, 2H), 1.47 (m, 4H), 1 .33 (m, 2H). HRMS (m/z): [M + H]⁺ calcd. for C₆HI₂NO, 118.1226; found, 118.1227.

References:

WO2022/229466,2022,A2 Location in patent:Page/Page column 58-59

67-56-1 Synthesis