Dichloromethane → 6-(N-methyl-N-phenylamino)hexyl chloride

Reaction equation

[CH3:1][N:2]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)[Cl:36]>>[CH3:1][N:2]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][Cl:36])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 11776Triphenylphosphine

HCID 152539786-[Methyl(phenyl)amino]hexan-1-OL

Product 1

HCID 540929106-(N-methyl-N-phenylamino)hexyl chloride

Procedure

1H-NMR (CDCl3,ppm) δ: 1.31-1.42(4 H,m), 1.51-1.63(4 H,m), 2.91(3 H,s), 3.30(2 H,t,J=7.9 Hz), 3.63(2 H,t,J=6.6 Hz), 6.64-6.70(3 H,m), 7.18-7.21(2 H,m) 6-(N-Methy-N-phenylamino)hexyl alcohol (1.1 g) and triphenylphosphine (1.3 g) were dissolved in methylene chloride (40 ml), and N-chlorosuccinylimide (0.71 g) was added, which was followed by stirring at room temperature for 1 hr 20 min. The organic layer was washed with brine, dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 0.90 g of 6-(N-methy-N-phenylamino)hexyl chloride.