N-(2-amino-2-methylpropyl)-2-phenylacetamide → 1-(4-Amino-3,5-dichlorophenyl)-2-[1,1-dimethyl-2-(2-phenylacetamido)ethylamino]ethanol dihydrochloride

HRID 223501Notes

Reaction equation

HRID 223501 reaction equation
O.[NH2:2][C:3]1[C:8]([Cl:9])=[CH:7][C:6]([C:10]([CH:12]=O)=[O:11])=[CH:5][C:4]=1[Cl:14].[CH3:15][C:16]([NH2:29])([CH3:28])[CH2:17][NH:18][C:19](=[O:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CO>[ClH:9].[ClH:9].[NH2:2][C:3]1[C:4]([Cl:14])=[CH:5][C:6]([CH:10]([OH:11])[CH2:12][NH:29][C:16]([CH3:28])([CH3:15])[CH2:17][NH:18][C:19](=[O:27])[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:7][C:8]=1[Cl:9]

Participants

4

Reactant 2

HCID 12876178N-(2-amino-2-methylpropyl)-2-phenylacetamideHCID 205215294-Amino-3,5-dichlorophenylglyoxal hydrate

Product 1

HCID 705403041-(4-Amino-3,5-dichlorophenyl)-2-[1,1-dimethyl-2-(2-phenylacetamido)ethylamino]ethanol dihydrochlorideYield 130.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-amino-3,5-dichlorophenylglyoxal hydrate (1.18 g.) and 1,1-dimethyl-2-(2-phenylacetamido)ethylamine (1.03 g.) in methanol (20 ml.) was stirred at room temperature for 16 hours. The mixture was then filtered and the filtrate stirred vigorously during the dropwise addition of a solution of sodium borohydride (500 mg.) in water (2 ml.). After stirring for 2 hours, the mixture was acidified with concentrated hydrochloric acid to pH 2-3, and then evaporated. The solid residue was suspended in water (50 ml.) and the suspension obtained was extracted with ether (100 ml). The aqueous phase was basified to pH 12-13 by addition of aqueous ammonia solution (density 0.88), and extracted with ether (2×100 ml.). The combined extracts were dried (MgSO4) and evaporated. The resultant oil was dissolved in propan-2-ol (5 ml.) and an ethereal solution of hydrogen chloride was added to bring the pH to 2-3. Further addition of an excess of dry ether gave a precipitate (1.05 g., 43%) of 1-(4-amino-3,5-di-chlorophenyl)-2-[1,1-dimethyl-2-(2-phenylacetamido)ethylamino]-ethanol dihydrochloride (Example 1), m.p. 105°-8° C.

Workup

  1. filtrationThe mixture was then filtered
  2. stirringthe filtrate stirred vigorously during the dropwise addition of a solution of sodium borohydride (500 mg.) in water (2 ml.)
  3. stirringAfter stirring for 2 hours
  4. customevaporated
  5. customthe suspension obtained
  6. extractionwas extracted with ether (100 ml)
  7. additionThe aqueous phase was basified to pH 12-13 by addition of aqueous ammonia solution (density 0.88)
  8. extractionextracted with ether (2×100 ml.)
  9. dry with materialThe combined extracts were dried (MgSO4)
  10. customevaporated
  11. dissolutionThe resultant oil was dissolved in propan-2-ol (5 ml.)
  12. additionan ethereal solution of hydrogen chloride was added
  13. additionFurther addition of an excess of dry ether

Sources & evidence

ORD record
ord-337f585733a14e62b6f91769aa7e30d9
Source dataset
uspto-grants-1982_10
Patent number
US04355045

Reaction notes

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