Hydrochloric Acid → Nitroso-N-methyl-N-(2-phenyl)ethylamine

HRID 1647177Notes

Reaction equation

HRID 1647177 reaction equation
Cl.[CH3:2][NH:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(O)C.Cl.[N:16]([O-])=[O:17].[Na+]>O>[CH3:2][N:3]([CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[N:16]=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 77742Phenethylamine, N-methyl-, hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 83271Nitroso-N-methyl-N-(2-phenyl)ethylamineYield 81.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

A sample of N-methyl-2-phenylethylamine hydrochloride (6.4 g, 37.3 mmol) was dissolved in water (18 ml), ethanol (11 ml) and 2N hydrochloric acid (4 ml) were introduced and the solution was heated to 70° C. A solution of sodium nitrite (2.6 g, 37.7 mmol) in water (11 ml) was added dropwise to the reaction mixture over 30 min. During the addition the reaction mixture was acidified with 2N hydrochloric acid (4 ml). Cooling was followed by extraction with n-heptane (4×100 ml); the combined extracts were dried (MgSO4) and evaporated in vacuo to provide the N-methyl-N-nitroso-2-phenylethylamine as an oil (5.0 g, 81%) (a ca. 65:35 mixture of apparent geometric isomers), 1H NMR (DMSO-d6) γ 2.98 (3H, s,--CH3), 3.05 (2H, t, PhCH2 --), 4.37 (2H, t, --CH2 --N--), 7.13-7.36 (5 H, m, Ar-H) (major isomer); 2.78 (2H, t, PhCH2 --), 2.98 (3H, s,--CH3), 3.77 (2H, t,--CH2 --N--), 7.13-7.36 (5H, m, Ar-H) (minor isomer).

Workup

  1. additionDuring the addition the reaction mixture
  2. temperatureCooling
  3. extractionwas followed by extraction with n-heptane (4×100 ml)
  4. dry with materialthe combined extracts were dried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-274a89d656df4755bbc9b3da8336bfa5
Source dataset
uspto-grants-1995_07
Patent number
US05430027

Reaction notes

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