Methylamine → trans-4-(3-Chlorophenyl)-but-3-enylamine

HRID 6719Notes

Reaction equation

HRID 6719 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[CH2:10][CH2:11][N:12]2C(=O)C3=CC=CC=C3C2=O)[CH:5]=[CH:6][CH:7]=1.CN>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:9]/[CH2:10][CH2:11][NH2:12])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 10710192trans-N-[4-(3-chlorophenyl)-but-3-enyl]-phthalimide

Product 1

HCID 22018476trans-4-(3-Chlorophenyl)-but-3-enylamineYield 68.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of trans-N-[4-(3-chlorophenyl)-but-3-enyl]-phthalimide (0.50 g) and methylamine (2 M in tetrahydrofuran, 8 mL) in 20 mL ethanol was heated to reflux for 4 h. The solution was cooled to rt and the solvent was removed in vacuo. The resulting residue was dissolved in ethyl acetate and extracted 3 times with 1 M hydrochloric acid. The combined acid layers were made basic with potassium hydroxide to pH 9 and extracted with ethyl acetate. The ethyl acetate layer was dried over sodium sulfate and the solvent was removed in vacuo to yield 0.20 g of trans-4-(3-chlorophenyl)-but-3-enylamine.

Workup

  1. temperatureto reflux for 4 h
  2. customthe solvent was removed in vacuo
  3. dissolutionThe resulting residue was dissolved in ethyl acetate
  4. extractionextracted 3 times with 1 M hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-3af9858d43a54428aca87fd4a926d00a
Source dataset
uspto-grants-2006_08
Patent number
US07084154B2

Reaction notes

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