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

HRID 2262490노트

반응식

HRID 2262490 반응식
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

참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 66934509Morpholin-2-ylmethyl 4-phenylpiperazine-1-carboxylate dihydrochloride salt2회

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b74ea0d626d74368928de04ce63d3667
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851471B2

반응 노트

불러오는 중…