Ammonia → HCID 53959586, compound

HRID 1462364Notes

Reaction equation

HRID 1462364 reaction equation
[NH3:1].[C:2]([C:6]1[CH:7]=[C:8]([CH:23]=[CH:24][C:25]=1[OH:26])[O:9][CH2:10][CH:11]([NH:13][CH2:14][CH:15]([OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:12])(OC)=[O:3]>O1CCOCC1>[C:2]([C:6]1[CH:7]=[C:8]([CH:23]=[CH:24][C:25]=1[OH:26])[O:9][CH2:10][CH:11]([NH:13][CH2:14][CH:15]([OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:12])(=[O:3])[NH2:1]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 54475721HCID 54475721, compound

Product 1

HCID 53959586HCID 53959586, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

20 ml of concentrated ammonia solution are added to a solution of 1.7 g of crude α-[N-[2-(3-carbomethoxy-4-hydroxy-phenoxy)-1-methyl-ethyl]-aminomethyl]-benzyl alcohol in 10 ml of dioxan and the mixture is left to stand at room temperature for 60-70 hours. The reaction mixture is evaporated, the residue is dissolved in 75 ml of ethyl acetate and the solution is washed with 10 ml of saturated, aqueous sodium chloride solution. Evaporation of the organic phase yields crude α-[N-[2-(3-carbamoyl-4-hydroxy-phenoxy)-1-methyl-ethyl]aminomethyl]-benzyl alcohol as a mixture of diastereoisomers in the form of an oil and the latter is crystallised from a little ethyl acetate and is identical to the product obtained, for example, in Example 1; melting point 120°-140°.

Workup

  1. waitthe mixture is left
  2. customThe reaction mixture is evaporated
  3. dissolutionthe residue is dissolved in 75 ml of ethyl acetate
  4. washthe solution is washed with 10 ml of saturated, aqueous sodium chloride solution
  5. customEvaporation of the organic phase

Sources & evidence

ORD record
ord-9c83767db7434cda88e71104bf60bf3a
Source dataset
uspto-grants-1984_07
Patent number
US04460580

Reaction notes

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