HCID 20066008, compound → HCID 67826849, compound

HRID 359057Notes

Reaction equation

HRID 359057 reaction equation
[ClH:1].[OH:2][CH:3]([CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:4][NH:5][CH2:6][CH2:7][C:8]1[CH:19]=[CH:18][C:11]([O:12][CH2:13][C:14]([O:16]C)=[O:15])=[CH:10][CH:9]=1>Cl>[ClH:1].[OH:2][CH:3]([CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:4][NH:5][CH2:6][CH2:7][C:8]1[CH:19]=[CH:18][C:11]([O:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:10][CH:9]=1

Participants

3

Reactant 1

HCID 20066008HCID 20066008, compound

Product 1

HCID 67826849HCID 67826849, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Methyl 4-[2-(2-hydroxy-3-phenoxypropylamino)ethyl]-phenoxyacetate hydrochloride (3.0 g) was suspended in 2N hydrochloric acid (150 ml) and heated on the steam bath for 2 hours. A clear solution was produced, from which the product crystallised on cooling. The crystals were filtered off, washed with a small volume of 2N hydrochloric acid followed by ether, and dried over phosphorus pentoxide. Thus was obtained 4-[2-(2-hydroxy-3-phenoxypropylamino)-ethyl]phenoxyacetic acid hydrochloride (2.04 g) mp 192°-94° C.; NMR 2.86-3.33[m,6H, CH2NHCH2CH2 ]: 4.02[m,2H, PhOCH2 ]; 4.22[m,1H,CHOH]; 4.63[s,2H, OCH2CO]; 6.84-7.38[m,9H, aromatic H]: microanalysis: found C, 59.8; H, 6.3; N, 3.5; Cl, 9.3%; C19H23NO5.HCl requires: C, 59.8; H, 6.3; N,3.7; Cl, 9.3 %.

Workup

  1. temperatureheated on the steam bath for 2 hours
  2. customA clear solution was produced, from which the product
  3. customcrystallised
  4. temperatureon cooling
  5. filtrationThe crystals were filtered off
  6. washwashed with a small volume of 2N hydrochloric acid
  7. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-bb002abc16334025b07f9d186b004586
Source dataset
uspto-grants-1991_03
Patent number
US04999377

Reaction notes

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