三乙胺 → N-[2-(4-bromophenyl)acetyl]-N-methyl-2-(1-piperidinyl)ethylamine

HRID 1279153

反应方程式

HRID 1279153 反应方程式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:16][NH:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C(N(CC)CC)C>C(Cl)(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([N:17]([CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH3:16])=[O:11])=[CH:6][CH:7]=1

参与物

7

反应物 4

HCID 8471三乙胺HCID 24386氯化亚砜HCID 74654对溴苯乙酸HCID 3157473N-甲基-2-(1-哌啶基)乙胺

产物 1

HCID 18668140N-[2-(4-bromophenyl)acetyl]-N-methyl-2-(1-piperidinyl)ethylamine收率 95.1%

试剂、催化剂与溶剂 2

HCID 6228N,N-二甲基甲酰胺催化剂HCID 6212三氯甲烷溶剂4 次

实验过程

To a solution of 4-bromophenylacetic acid (10 g, 46.5 mmol) in CHCl3, (100ml) was added thionyl chloride (8 ml) in CHCl3 (10 ml) and three drops of DMF. The mixture was reflux for one to two hours. The volatiles were removed in vacuo to give a light yellow oil. This acid chloride was dissolved in CHCl3 30 ml and added dropwise to another flask containing N-methyl-2-(1-piperidinyl)ethyl amine (6.1 g, 48 mmol) and triethylamine (25 ml) and CHCl3 (100 ml) at 0° C. The reaction mixture was stirred overnight at room. The volatiles were removed, the residue dissolved in CHCl3 (150 ml) and washed with (2×100 ml) water and 2% NaHCO3 (50 ml). The organic layer was dried and the volatiles were removed to give a light yellow oil (15.0 g). The oil was passed through a silica gel column and eluted with CHCl3/MeOH to give 13 g, (87%) of the desired pure compound. 1H NMR 1.30-1.54 (m, 6H, piperidinyl CH2); 2.33-2.43 (m, 6H, NCH2); 2.92 (44%), 2.96 (56%) (s, 3H, N—Me); 3.32-3.37 (46%), 3.45-3.49 (54%), (t, 2H, J=7.1 Hz, NCH2); 3.61 (56%), 3.67 (44%), (s, 2H, benzylic); 7.09-7.11 (d, 2H, arom); 7.38-7.41 (d, 2H, arom).

后处理

  1. temperatureThe mixture was reflux for one to two hours
  2. customThe volatiles were removed in vacuo
  3. customto give a light yellow oil
  4. additionadded dropwise to another flask
  5. customThe volatiles were removed
  6. dissolutionthe residue dissolved in CHCl3 (150 ml)
  7. washwashed with (2×100 ml) water and 2% NaHCO3 (50 ml)
  8. customThe organic layer was dried
  9. customthe volatiles were removed

来源与证据

ORD记录
ord-9fef631385e244fba295cbb31d3022b4
来源数据集
uspto-grants-2002_09
专利号
US06447748B1

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