반응 #1772043

반응 방정식

Hunig's base

3-bromobenzyl bromide

N-methyl-β-alanine nitrile

→

3-((3-bromobenzyl)(methyl)amino)-propanenitrile

수율 116.9%

용매

DMF

반응 조건

후처리

1. 1
   농축concentrated in vacuo
2. 2
   기타triturated with ether/EtOAc
3. 3
   여과filtered
4. 4
   기타[A second reaction
5. 5
   농축The combined filtrates were concentrated by rotory evaporation
6. 6
   workup.ADDITIONthe residue was charged (CH2Cl2) to a 65 (M) Biotage® silica gel column
7. 7
   세척Segment 1: Gradient elution from 5-15% B over 1.3 L

실험 절차

Hunig's base (26.5 mL, 0.15 mol) was added to 3-bromobenzyl bromide (38 g, 0.15 mol) and N-methyl-β-alanine nitrile (14.2 mL, 0.15 mol) in dry DMF (400 mL). The solution was stirred 16 h, concentrated in vacuo to near dryness, triturated with ether/EtOAc, and filtered. [A second reaction was repeated on 12 g]. The combined filtrates were concentrated by rotory evaporation and the residue was charged (CH2Cl2) to a 65 (M) Biotage® silica gel column; Segment 1: Gradient elution from 5-15% B over 1.3 L; Segment 2: 15%-100% B (A=Hexanes; B=EtOAc) over 6.75 L to give Example 4, 3-((3-bromobenzyl)(methyl)amino)-propanenitrile 44.4 g (88%). 1H NMR (500 MHz, DMSO-d6) δ 7.54 (s, 1H), 7.46 (d, J=7.6 Hz, 1H), 7.34 (d, J=7.6 Hz, 1H), 7.30 (t, J=7.6 Hz, 1H), 3.54 (s, 2H), 2.71 (t, J=6.4 Hz, 2H), 2.63 (t, J=6.4 Hz, 2H), 2.17 (s, 3H). RT=1.1 minutes (condition 2); LRMS: Anal. Calcd. for C11H13BrN2: 253.03. found: 253.05 (M+H).

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