3-Chloropropyl(diethyl)amine → HCID 10064795, compound

HRID 1414607Notes

Reaction equation

HRID 1414607 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[CH:12]=2)=[CH:4][CH:3]=1.C[O-].[Na+].[Na].[CH2:21]([N:23]([CH2:26][CH2:27][CH2:28]Cl)[CH2:24][CH3:25])[CH3:22]>CO.C1(C)C=CC=CC=1>[CH2:21]([N:23]([CH2:24][CH3:25])[CH2:26][CH2:27][CH2:28][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[CH:12]=2)=[CH:4][CH:3]=1)[CH3:22]

Participants

7

Reactant 4

HCID 669183-Chloropropyl(diethyl)amineHCID 5360545SodiumHCID 101251634-(1-Benzofuran-2-yl)phenolHCID 10942334Sodium Methoxide

Product 1

HCID 10064795HCID 10064795, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 1140TolueneSolvent

Procedure

A solution of 4.9 g. (0.023 mol.) of 2-p-hydroxyphenylbenzofuran in 75 ml. of toluene and 5 ml. of methanol was added to a sodium methoxide solution prepared by dissolving 0.54 g. (0.023 g.-atom) of sodium in 25 ml. of methanol. The mixture was refluxed for 15 minutes, then the methanol was removed by distillation and 3.48 g. (0.023 mol.) of diethylaminopropyl chloride was added and the resulting reaction mixture was refluxed for four hours. The mixture was filtered and the filtrate concentrated under reduced pressure to give 2-[4'-(3-diethylaminopropoxy)phenyl]benzofuran, m.p. 86°-88°.

Workup

  1. customprepared
  2. dissolutionby dissolving 0.54 g
  3. temperatureThe mixture was refluxed for 15 minutes
  4. customthe methanol was removed by distillation and 3.48 g
  5. customthe resulting reaction mixture
  6. temperaturewas refluxed for four hours
  7. filtrationThe mixture was filtered
  8. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-326e4205cc1f492192a1ea104b791716
Source dataset
uspto-grants-1977_01
Patent number
US04001426

Reaction notes

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