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

HRID 1279153

反応式

HRID 1279153 の反応式
[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

参加物

7

反応物 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 74654Benzeneacetic acid, 4-bromo-HCID 3157473Methyl(2-(piperidin-1-yl)ethyl)amine

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6212Chloroform溶媒4 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9fef631385e244fba295cbb31d3022b4
出典データセット
uspto-grants-2002_09
特許番号
US06447748B1

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