Methylhydrazine → 1-benzyl-1-methylhydrazine

HRID 1197394Notes

Reaction equation

HRID 1197394 reaction equation
[CH3:1][NH:2][NH2:3].[CH2:4](Br)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>ClCCl>[CH2:4]([N:2]([CH3:1])[NH2:3])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Procedure

Methylhydrazine (0.1 ml, 2.0 mmol) in dichloromethane (5 ml) was treated dropwise with a solution of benzyl bromide (0.12 ml, 1.0 mmol) in dichloromethane (2 ml). After addition was complete the mixture was stirred for 10 min. and evaporated to dryness under reduced pressure. The residue was diluted with brine (5 ml) and ethyl acetate (5 ml). The organic phase was separated, dried over magnesium sulphate and evaporated to dryness under reduced pressure to give N-benzyl-N-methylhydrazine (0.082 g, 60%); υmax (CH2Cl2) 1650 cm-1 ; δH (CDCl3) 2.49 (3H, s), 3.41 (2H, s), 3.60 (2H, s), and 7.27 (5H, s).

Workup

  1. additionAfter addition
  2. customevaporated to dryness under reduced pressure
  3. additionThe residue was diluted with brine (5 ml) and ethyl acetate (5 ml)
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulphate
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-b2e0845dc82f4cd998a8ecb725d54cbd
Source dataset
uspto-grants-1994_01
Patent number
US05275816

Reaction notes

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