Formaldehyde → (4-Methylmorpholin-2-yl)methyl 4-phenylpiperazine-1-carboxylate

HRID 2262490ノート

反応式

HRID 2262490 の反応式
Cl.Cl.[C:3]1([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH:19]3[O:24][CH2:23][CH2:22][NH:21][CH2:20]3)=[O:16])[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C=O.O.[C:28](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[C:3]1([N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH:19]3[O:24][CH2:23][CH2:22][N:21]([CH3:28])[CH2:20]3)=[O:16])[CH2:11][CH2:10]2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

6

反応物 4

HCID 712FormaldehydeHCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 66934509Morpholin-2-ylmethyl 4-phenylpiperazine-1-carboxylate dihydrochloride salt2 回

生成物 1

HCID 42634003(4-Methylmorpholin-2-yl)methyl 4-phenylpiperazine-1-carboxylate収率 89%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Morpholin-2-ylmethyl 4-phenylpiperazine-1-carboxylate (non-HCl salt of Example 10; 1.00 g, 3.27 mmol) and 37% formaldehyde in water (1.97 g, 1.82 mL, 65.5 mmol) were dissolved in MeOH (20 mL) at room temperature followed by addition of sodium triacetoxyborohydride (2.78 g, 13.1 mmol) portionwise over 5 minutes. The reaction mixture was stirred for 2 h. The reaction mixture was quenched by the addition of saturated aq Na2CO3 solution. The solvents were removed in vacuo and the residual aqueous phase was loaded onto an Isolute HM-N 20 mL cartridge. The desired product was eluted with DCM (200 mL) and the solvent removed in vacuo to give (4-methylmorpholin-2-yl)methyl 4-phenylpiperazine-1-carboxylate (0.93 g, 88.9%) as a colourless gum.

後処理

  1. customThe reaction mixture was quenched by the addition of saturated aq Na2CO3 solution
  2. customThe solvents were removed in vacuo
  3. washThe desired product was eluted with DCM (200 mL)
  4. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-b74ea0d626d74368928de04ce63d3667
出典データセット
uspto-grants-2010_12
特許番号
US07851471B2

反応ノート

読み込み中…