2-[(3-Nitrophenoxy)methyl]oxirane → 1-(3-Aminophenoxy)-3-[2-(4-carbamoylphenoxy)ethylamino]propan-2-ol

HRID 1657633Notes

Reaction equation

HRID 1657633 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[O:7][CH2:8][CH:9]([OH:24])[CH2:10][NH:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:23])[NH2:22])=[CH:17][CH:16]=1)([O-])=O.[H][H].[N+](C1C=C(C=CC=1)OCC1OC1)([O-])=O.C(C1C=CC(OCCN)=CC=1)(=O)N>[Pt]=O.CO>[NH2:1][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][CH:27]=1)[O:7][CH2:8][CH:9]([OH:24])[CH2:10][NH:11][CH2:12][CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:23])[NH2:22])=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 2193452-[(3-Nitrophenoxy)methyl]oxiraneHCID 126663984-(2-Aminoethoxy)benzamideHCID 215350331-(3-Nitrophenoxy)-3-[2-(4-carbamoylphenoxy)ethylamino]propan-2-olHCID 178418361HCID 178418361, compound

Product 1

HCID 215350231-(3-Aminophenoxy)-3-[2-(4-carbamoylphenoxy)ethylamino]propan-2-ol

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

A solution consisting of 12 g. of 1-(3-nitrophenoxy)-3-[2-(4-carbamoylphenoxy)ethylamino]propan-2-ol (m.p. 127°-129°C.) dissolved in 1000 ml. of methanol was subjected to catalytic hydrogenation over 0.3 g. of platinum oxide at room temperature (~25°C.) and 50 p.s.i. pressure of hydrogen [the 3-nitro starting material was prepared according to the procedure of Example VII from 1-(3-nitrophenoxy)-2,3-epoxypropane and 2-(4-carbamoylphenoxy)ethylamine]. Upon completion of this step, the resultant mixture was filtered and the clear filtrate thereafter evaporated to dryness while under reduced pressure to afford a white residual solid. Recrystallization of the latter material from methanol then gave pure 1-(3-aminophenoxy)-3-[2-(4-carbamoylphenoxy)ethylamino]propan-2-ol, m.p. 149°-157°C.

Workup

  1. customat room temperature
  2. custom(~25°C.) and 50 p.s.i
  3. filtrationUpon completion of this step, the resultant mixture was filtered
  4. customthe clear filtrate thereafter evaporated to dryness while under reduced pressure
  5. customto afford a white residual solid
  6. customRecrystallization of the latter material from methanol

Sources & evidence

ORD record
ord-f4a9c8ea54e549c9a579b641b1bc1a77
Source dataset
uspto-grants-1976_06
Patent number
US03961072

Reaction notes

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