Sodium cyanoborohydride → 1-(4-Amino-3,5-dichlorophenyl)-2-[1,1-dimethyl-2-(2-phenylacetamido)ethylamino]ethanol dihydrochloride

HRID 223504Notes

Reaction equation

HRID 223504 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.C([BH3-])#N.[Na+]>C(#N)C.C(O)(=O)C>[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

6

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 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 174.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-amino-3,5-dichlorophenylglyoxal hydrate (2.35 g.) and 1,1-dimethyl-2-(2-phenylacetamido)ethylamine (2.06 g.) in acetonitrile (50 ml.) and acetic acid (3 ml.) was stirred for 30 minutes. Sodium cyanoborohydride (1.26 g.) was then added to the reaction mixture in portions over 5 minutes. After 16 hours of stirring the mixture was evaporated and the residue was partitioned between 10% v/v aqueous acetic acid (100 ml.) and ethyl acetate (100 ml.). The organic phase was separated, dried (MgSO4) and evaporated. The semi-solid residue was dissolved in propan-2-ol (10 ml.) and ethereal hydrogen chloride was added to bring the pH to 2-3. Addition of dry ether then gave a precipitate (2.8 g., 63%) of 1-(4-amino-3,5-dichlorophenyl)-2-[1,1-dimethyl-2-(2-phenylacetamido)ethylamino]ethanol dihydrochloride m.p. 105°-108° C.

Workup

  1. stirringAfter 16 hours of stirring the mixture
  2. customwas evaporated
  3. customthe residue was partitioned between 10% v/v aqueous acetic acid (100 ml.) and ethyl acetate (100 ml.)
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. dissolutionThe semi-solid residue was dissolved in propan-2-ol (10 ml.)
  8. additionethereal hydrogen chloride was added
  9. additionAddition of dry ether

Sources & evidence

ORD record
ord-bc54c6532be94aa2b3a986cf27aaaadd
Source dataset
uspto-grants-1982_10
Patent number
US04355045

Reaction notes

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