3,4-Dichlorophenethylamine → (s)-1-(2-Nitrophenoxy)-3-(3,4-dichlorophenylethylamino)-2-propanol

HRID 2223429Notes

Reaction equation

HRID 2223429 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][C@H:12]1[O:14][CH2:13]1)([O-:3])=[O:2].[Cl:15][C:16]1[CH:17]=[C:18]([CH2:23][CH2:24][NH2:25])[CH:19]=[CH:20][C:21]=1[Cl:22]>C(O)C>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][C@@H:12]([OH:14])[CH2:13][NH:25][CH2:24][CH2:23][C:18]1[CH:19]=[CH:20][C:21]([Cl:22])=[C:16]([Cl:15])[CH:17]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 2179583,4-DichlorophenethylamineHCID 12619675(S)-2-((2-Nitrophenoxy)methyl)oxirane

Product 1

HCID 59715535(s)-1-(2-Nitrophenoxy)-3-(3,4-dichlorophenylethylamino)-2-propanolYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Compound 17a-S (1.05 g, 5.4 mmol) and 3,4-dichloropenylethylamine (1.02 g, 0.8 ml, 5.4 mmol) were dissolved in 25 ml ethanol and refluxed for 12 hours. Then the solvent was evaporated and the residue recrystallized from ethylacetate-petroleum ether to give the product (1.02 g, 99% yield, m.p. 73-74° C.) as a white solid.

Workup

  1. temperaturerefluxed for 12 hours
  2. customThen the solvent was evaporated
  3. customthe residue recrystallized from ethylacetate-petroleum ether

Sources & evidence

ORD record
ord-85566c0ecced44268890c2f44ecc94fd
Source dataset
uspto-grants-2008_05
Patent number
US07375136B2

Reaction notes

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