Methylhydrazine → HCID 14814215, compound

HRID 1089257Notes

Reaction equation

HRID 1089257 reaction equation
[CH3:1][O:2][C:3]1[CH:36]=[CH:35][C:6]([CH2:7][O:8][CH2:9][CH:10]([O:23][N:24]2C(=O)C3=CC=CC=C3C2=O)[CH2:11][CH2:12][O:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.CNN>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][CH2:9][CH:10]([O:23][NH2:24])[CH2:11][CH2:12][O:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 6061Methylhydrazine2×HCID 14814214HCID 14814214, compound

Product 1

HCID 14814215HCID 14814215, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[1,4-bis(4-methoxybenzyloxy)but-2-oxy]phthalimide (10.3 g, 21 mmol) in dichloromethane (80 ml) was added methylhydrazine (1.49 ml, 28 mmol) and the solution was stirred at room temperature. After 20 minutes, further methylhydrazine (0.22 ml) was added. After a further 20 minutes the solution was filtered and the filtrate was extracted with aqueous sodium carbonate (3%). The organic layer was dried (magnesium sulphate) and the solvent removed. The residue was purified by column chromatography on silica gel eluting with hexane-ethyl acetate (1:1) to afford 1,4-bis(4-methoxybenzyloxy)but-2-oxyamine as a clear colourless oil (5.16 g, 68%). IR: υmax (film) 2860, 1615, 1515 and 1250 cm-1 ; 1H NMR: δH (CDCl3) 1.80 (2H, m, 3-H), 3.54 (4H, m, 1-H and 4-H), 3.80 (6H, s, 2×CH3), 3.86 (1H, m, 2-H), 4.42 (2H, s, ArCH2), 4.48 (2H, s, ArCH2), 5.37 (2H, s, D2O exchangeable, NH2), 6.87 (4H, m, Ar-H) and 7.25 (4H, m, Ar-H).

Workup

  1. filtrationAfter a further 20 minutes the solution was filtered
  2. extractionthe filtrate was extracted with aqueous sodium carbonate (3%)
  3. dry with materialThe organic layer was dried (magnesium sulphate)
  4. customthe solvent removed
  5. customThe residue was purified by column chromatography on silica gel eluting with hexane-ethyl acetate (1:1)

Sources & evidence

ORD record
ord-fdf6b93d23ae4f728427236e7b50c6d1
Source dataset
uspto-grants-1990_10
Patent number
US04965270

Reaction notes

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