Sodium hydride → HCID 54179641, compound

HRID 361713Notes

Reaction equation

HRID 361713 reaction equation
[H-].[Na+].[CH2:3]([C:6]1[CH:11]=[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:9]=[CH:8][C:7]=1[OH:17])[CH:4]=[CH2:5].[CH3:18][N:19]([CH3:24])[CH2:20][CH2:21][CH2:22]Cl>C1(C)C=CC=CC=1>[CH3:18][N:19]([CH2:20][CH2:21][CH2:22][O:17][C:7]1[CH:8]=[CH:9][C:10]([O:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:11][C:6]=1[CH2:3][CH:4]=[CH2:5])[CH3:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 24770420HCID 24770420, compound

Product 1

HCID 54179641HCID 54179641, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Sodium hydride (106 mg) was added to a solution of 2-allyl-4-butoxyphenol (500 mg) in toluene (40 ml). The reaction mixture was heated to reflux. A solution of 3-dimethylaminopropyl chloride (437 mg) in toluene (20 ml) was added to the refluxing reaction mixture and heating continued for a further 8 hours. The reaction mixture was cooled to ambient temperature, evaporated and the residue dissolved in water (10 ml). The resulting solution was extracted with ethyl acetate (4×15 ml). The ethyl acetate extracts were combined, dried (MgSO4) and evaporated to give an oil which was further purified by flash column chromatography on silica gel (Merck Art No 9385) using a 50:50:0.1 mixture of ethyl acetate, hexane and triethylamine as eluent to give N,N-dimethyl-3-(2-allyl-4-butoxyphenoxy)propylamine as yellow oil (556 mg); microanalysis, found: C, 74.5; H, 10.2; N, 4.8% C18H29NO2 requires: C, 74.2; H, 10.0; N, 4.8%; NMR([CD3 ]2SO): 0.91(3H,t), 1.42(2H,m), 1.65(2H,m), 1.82(2H,m), 2.15(6H,s), 2.38(2H,t), 3.27(2H,d), 3.88(4H,m), 5.2(2H,m), 5.92(1H,m), 6.7(2H,m) and 6.82(1H,m); m/z 292(M+H).

Workup

  1. temperatureThe reaction mixture was heated to reflux
  2. temperatureheating
  3. customevaporated
  4. dissolutionthe residue dissolved in water (10 ml)
  5. extractionThe resulting solution was extracted with ethyl acetate (4×15 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customto give an oil which
  9. customwas further purified by flash column chromatography on silica gel (Merck Art No 9385)
  10. additiona 50:50:0.1 mixture of ethyl acetate, hexane and triethylamine as eluent

Sources & evidence

ORD record
ord-d528bde63d42456d9375c11e9dee3918
Source dataset
uspto-grants-1999_02
Patent number
US05866611

Reaction notes

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