Chloroform → 2-[(4-Methylpiperazin-1-yl)methyl]morpholine

HRID 2112764Notes

Reaction equation

HRID 2112764 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[CH2:12][CH2:11][O:10][CH:9]([CH2:13][N:14]2[CH2:19][CH2:18][N:17]([C:20](OC(C)(C)C)=O)[CH2:16][CH2:15]2)[CH2:8]1.[OH-].[Na+].C(Cl)(Cl)Cl>O1CCCC1>[CH3:20][N:17]1[CH2:16][CH2:15][N:14]([CH2:13][CH:9]2[O:10][CH2:11][CH2:12][NH:7][CH2:8]2)[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23079694Tert-butyl 4-(morpholin-2-ylmethyl)piperazine-1-carboxylate

Product 1

HCID 146275682-[(4-Methylpiperazin-1-yl)methyl]morpholineYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

Lithium aluminum hydride (150 mg, 4.10 mmol) was suspended in tetrahydrofuran (5 mL), and the suspension was mixed with a solution of tert-butyl 4-morpholin-2-ylmethylpiperazinecarboxylate (390 mg, 1.37 mmol) prepared as an intermediate according to Process Step 2 of Reference Example 19 in tetrahydrofuran (5 mL) added dropwise under ice-cooling, followed by heating at 60° C. under reflux for two hours. An aqueous sodium hydroxide solution (2 mol/L, 10 mL) and chloroform (50 mL) were added under ice-cooling, followed by separation. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure, to thereby yield the title compound (180 mg, in a yield of 66%).

Workup

  1. customprepared as an intermediate
  2. additionadded dropwise under ice-
  3. temperaturecooling
  4. temperatureunder reflux for two hours
  5. temperaturecooling
  6. customfollowed by separation
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-fe6286ce9ecd46428d1b775860ddaf95
Source dataset
uspto-grants-2009_04
Patent number
US07524852B2

Reaction notes

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