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

HRID 344242Notes

Reaction equation

HRID 344242 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

4

Reactant 3

HCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 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.

Workup

  1. washThe organic layer was washed with brine
  2. customdried
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8c82d2f15b33429d87815a8abae89c22
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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