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

HRID 232586Notes

Reaction equation

HRID 232586 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-14c98c6e1bbb4dc59ef04e3a1d9bdc81
Source dataset
uspto-grants-1997_01
Patent number
US05591737

Reaction notes

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