Hydrochloric Acid → 1-(4-Methoxyphenyl)-2-methylpropan-2-amine--hydrogen chloride (1/1)

HRID 602052Notes

Reaction equation

HRID 602052 reaction equation
[CH3:1][C:2]([NH2:13])([CH3:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1.[ClH:14]>COC(C)(C)C.O1CCOCC1>[ClH:14].[CH3:12][C:2]([NH2:13])([CH3:1])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 918922-(4-Methoxyphenyl)-1,1-dimethylethylamine

Product 1

HCID 918911-(4-Methoxyphenyl)-2-methylpropan-2-amine--hydrogen chloride (1/1)Yield 92%

Reagents, catalysts & solvents 2

HCID 15413tert-Butyl methyl etherSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

2-Methyl-1-(4-methoxyphenyl)-2-propanamine (19.0 g, 0.10 mol) was dissolved in tert-butyl methyl ether (200 mL) and cooled to 0° C. A solution of 1.3 M HCl in 1,4-dioxane (85 mL) was added through an addition funnel over a period of 10 min. After the addition was complete, stirring was continued for additional 20 min at 0° C. The resulting precipitate was collected by filtration through a sintered glass funnel. The solid was washed with tert-butyl methyl ether (3×50 mL), and dried in vacuum oven for 30 h at 40° C. to afford 21.0 g (92%) of 2-methyl-1-(4-methoxyphenyl)-2-propanamine hydrochloride as a white solid; 1H NMR (200 MHz, DMSO-d6) δ 7.14 (d, J=8.4 Hz, 2H), 6.88 (d, J=8.4 Hz, 2H), 3.72 (s, 3H), 2.80 (s, 2H), 1.17 (s, 6H); 13C NMR (50 MHz, DMSO-d6) δ 158.1, 131.4, 127.2, 113.6, 54.9, 53.7, 44.1, 24.6; ESI MS m/z 180 [C11H17NO+H]+.

Workup

  1. additionAfter the addition
  2. filtrationThe resulting precipitate was collected by filtration through a sintered glass funnel
  3. washThe solid was washed with tert-butyl methyl ether (3×50 mL)
  4. customdried in vacuum oven for 30 h at 40° C.

Sources & evidence

ORD record
ord-5cf2239a681a446b8294613ce76de4ca
Source dataset
uspto-grants-2011_03
Patent number
US07902394B2

Reaction notes

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