Hydrochloric Acid → 2-(1-Methyl-2-(3-nitrophenyl)ethyl]ethylamine hydrochloride

HRID 429816Notes

Reaction equation

HRID 429816 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11](=O)[CH3:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[ClH:14].C(N)C.C([N:20]([CH2:23][CH3:24])CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>ClCCl.C(OCC)C.CO>[ClH:14].[CH3:12][CH:11]([CH2:24][CH2:23][NH2:20])[CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 11198Ethylamine hydrochloride2×HCID 5049666Sodium triacetoxyborohydrideHCID 125079341-(3-Nitrophenyl)propan-2-one

Product 1

HCID 602050972-(1-Methyl-2-(3-nitrophenyl)ethyl]ethylamine hydrochlorideYield 85%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (50 ml) was combined 1-(3-nitrophenyl)propan-2-one (1.44 grams, 8 mmole), ethylamine hydrochloride (0.42 grams, 8 mmole), and triethylamine (1.1 ml, 11 mmole). The mixture was stirred under nitrogen at room temperature for 30 minutes. Then sodium triacetoxyborohydride (2.5 grams, 11.7 mmole) was added in one portion. The mixture was stirred under nitrogen 18 hours. Additional ethylamine hydrochloride (0.4 grams) was added. After another 18 hours the mixture was diluted with ethyl ether, washed with 10% sodium hydroxide solution (50 ml), dried over anhydrous magnesium sulfate and the solvent removed under vacuum to give an oil. This oil was taken up into methanol, acidified with 1M hydrochloric acid in ether and the salt was precipitated by further addition of ether. The resulting solid was filtered and air dried to give [2-(1-methyl-2-(3-nitrophenyl)ethyl]ethylamine hydrochloride (1.4 grams, 85%), m.p. 173-175° C., M+H 208.

Workup

  1. stirringThe mixture was stirred under nitrogen 18 hours
  2. washwashed with 10% sodium hydroxide solution (50 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent removed under vacuum
  5. customto give an oil
  6. customthe salt was precipitated by further addition of ether
  7. filtrationThe resulting solid was filtered
  8. customair dried

Sources & evidence

ORD record
ord-23c4c77be53b40cbab5dcfa096471b31
Source dataset
uspto-grants-2001_11
Patent number
US06319920B1

Reaction notes

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