Borane;tetrahydrofuran → Hexahydro-N-methyl-1H-1,4-diazepine-1-ethanamine

HRID 1288828Notes

Reaction equation

HRID 1288828 reaction equation
[CH:1]([NH:3][CH2:4][CH2:5][N:6]1[CH2:12][CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=O.B.C1COCC1>C1COCC1>[CH3:1][NH:3][CH2:4][CH2:5][N:6]1[CH2:12][CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 18924841HCID 18924841, compound

Product 1

HCID 18924839Hexahydro-N-methyl-1H-1,4-diazepine-1-ethanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.75 gm of N-(2-formamidoethyl)homopiperazine in 20 ml of dry THF under N2 is added carefully 60 ml of borane THF solution. After the addition is complete the reaction mixture is heated to reflux for 5 hours then stirred at room temperature overnight. The reaction mixture is quenched by the careful addition of 20 ml of 6N HCl followed by refluxing for 1 hour. The reaction mixture is cooled, 50 ml of water added and solid KOH added carefully to alkaline pH. Extraction with ether gives the desired product N-(2-methylamino)homopiperazine.

Workup

  1. additionAfter the addition
  2. temperatureis heated
  3. temperatureto reflux for 5 hours
  4. customThe reaction mixture is quenched by the careful addition of 20 ml of 6N HCl
  5. temperatureby refluxing for 1 hour
  6. temperatureThe reaction mixture is cooled
  7. addition50 ml of water added
  8. additionsolid KOH added carefully
  9. extractionExtraction with ether

Sources & evidence

ORD record
ord-621ac7fd636f4d7f90a5c09791ef57b4
Source dataset
uspto-grants-1998_05
Patent number
US05747485

Reaction notes

Loading…