Water → N-[3-(4-methylphenyl)propyl]-2-(2-benzofuranyl)-2-hydroxyethanamine

HRID 1388739Notes

Reaction equation

HRID 1388739 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]([OH:13])[CH2:11][NH2:12].[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:17][CH:16]=1.C(N(CC)CC)C.O>CS(C)=O>[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][CH2:23][NH:12][CH2:11][CH:10]([C:2]2[O:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[CH:3]=2)[OH:13])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 128143572-Amino-1-(1-benzofuran-2-yl)ethan-1-olHCID 539033013-(4-Methylphenyl)propyl 4-methylbenzene-1-sulfonate

Product 1

HCID 12816509N-[3-(4-methylphenyl)propyl]-2-(2-benzofuranyl)-2-hydroxyethanamine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 2-(2-benzofuranyl)-2-hydroxyethanamine (1.75 g), 3-(4-methylphenyl)-1-(4-methylphenylsulphonyloxy) propane (3.0 g) and triethylamine (1.5 g) was stirred in dimethylsulphoxide for 2 days at ambient temperature. The mixture was poured into water, extracted with ether and the ether layers dried. Removal of the solvent gave an oil which was crystallised and recrystallised from ether to give N-[3-(4-methylphenyl)propyl]-2-(2-benzofuranyl)-2-hydroxyethanamine m.p. 118°-119°.

Workup

  1. extractionextracted with ether
  2. dry with materialthe ether layers dried
  3. customRemoval of the solvent
  4. customgave an oil which
  5. customwas crystallised
  6. customrecrystallised from ether

Sources & evidence

ORD record
ord-d2a087c8d85f4801a77085a20c21022e
Source dataset
uspto-grants-1984_02
Patent number
US04432993

Reaction notes

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