Hydrochloric Acid → HCID 53892805, compound

HRID 361712Notes

Reaction equation

HRID 361712 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:10][C:9]=1[CH2:19][CH:20]=[CH2:21])[CH3:3].[OH-:22].[Na+].OO.Cl>O1CCCC1.CCOCC.C(O)C>[CH3:1][N:2]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:10][C:9]=1[CH2:19][CH2:20][CH2:21][OH:22])[CH3:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 54179641HCID 54179641, compound

Product 1

HCID 53892805HCID 53892805, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of N,N-dimethyl-3-(2-allyl-4-butoxyphenoxy)propylamine (1.8 g) in tetrahydrofuran (3 ml) was added dropwise over a period of 3 minutes to a solution of borane tetrahydrofuran complex (1M, 12.4 ml) at a temperature of 0° C. and under an atmosphere of argon. The reaction mixture was stirred at 0° C. for 3 hours. Ethanol (10 ml) was added to the reaction mixture, followed by aqueous 6N aqueous sodium hydroxide and hydrogen peroxide solution (30%, 12 ml). The mixture was then heated at 50° C. for 1.5 hours. The reaction mixture was cooled to ambient temperature, extracted with ethyl acetate, the ethyl acetate extracts dried (MgSO4) and evaporated. The residue was purified by flash column chromatography on silica gel (Merck Art No 9385) using a 40:60:0.2 mixture of ethyl acetate, hexane and triethylamine as eluent to give an oil. The oil was dissolved in ether and excess ethereal hydrogen chloride added until crystallisation began. The solid was collected by filtration and dried to give N,N-dimethyl-3-[4-butoxy-2-(3-hydroxypropyl)phenoxy]propylamine as a white solid (60 mg), m.p. 118° C.; microanalysis, found: C, 62.4; H, 9.6; N, 4.0% C18H32NO3Cl requires: C, 62.5; H, 9.32; N, 4.05%; NMR ([CD3 ]2SO+CD3COOD): 0.95(3H,t), 1.45(2H,m), 1.7(4H,m), 2.2(2H,m), 2.58(2H,t), 2.89(6H,s), 3.35(2H,t), 3.55(2H,t), 3.9(2H,t), 4.02(2H,t), 6.72(2H,m) and 6.82(1H,s); m/z 310(M+H).

Workup

  1. temperatureThe mixture was then heated at 50° C. for 1.5 hours
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. extractionextracted with ethyl acetate
  4. dry with materialthe ethyl acetate extracts dried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by flash column chromatography on silica gel (Merck Art No 9385)
  7. additiona 40:60:0.2 mixture of ethyl acetate, hexane and triethylamine as eluent
  8. customto give an oil
  9. filtrationThe solid was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-f9ed891c5e364f3189a46d66851ef6c8
Source dataset
uspto-grants-1999_02
Patent number
US05866611

Reaction notes

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