No renderable structure data available
COC1=C(C=C(C=C1)CCCN)OCChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 3-(3,4-dimethoxyphenyl)propan-1-amine |
|---|---|
| IUPAC Name | — |
| CAS Number | 14773-42-3 |
| Database ID | 2281053 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
3-(3,4-dimethoxyphenyl)propan-1-amine (CAS 14773-42-3) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 2281053
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a4230ea099a342c4bd4c2ef7df4cf42aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3,4-Dimethoxycinnamonitrile (5 g) was dissolved in a mixture of EtOH (100 mL) and conc. HCl (10 mL) and hydrogenated with 10% Pd/C (wet, Degussa Type E101, Aldrich) at 65 psi on a Pan shaker for 70 h. The reaction mixture was filtered over Celite and the filtrate was concentrated to remove most of the EtOH. The residue was extracted twice with Et2O (discarded) and then cooled with ice and made strongly basic with 10 M aq. NaOH solution. The basic aqueous layer was extracted with Et2O and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 3-(3,4-dimethoxyphenyl)propylamine (5.07 g) as a pale yellow oil. 1H-NMR (300 MHz, CDCl3): δ=6.68-6.78 (m, 3H), 3.83 (s, 3H, OMe), 3.82 (s, 3H, OMe), 2.70 (t, J=7.0 Hz, 2H), 2.58 (t, J=7.2 Hz, 2H), 1.70-1.75 (m, 2H), 1.17 (broad s, 2H, NH2). The reaction mixture was filtered over Celite the filtrate was concentrated to remove most of the EtOH The residue was extracted twice with Et2O (discarded) cooled with ice The basic aqueous layer was extracted with Et2O the organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure
Source ID: ord-4ee089a2a3944c64b87f7de8413f434fConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 6.4 g of 3-(3,4-dimethoxyphenyl)-propylamine (0.03 moles) was refluxed with 5.47 g of phthalic anhydride (0.037 moles) in 70 ml of acetic acid for 2.5 hours. The solvent was then removed in the rotary evaporator. Recrystallization of the residue from 150 ml of ether gave 4.0 g of a first crop, m.p. 82°-85° and 7.0 g of a second crop, m.p. 81°-83°. The solvent was then removed in the rotary evaporator Recrystallization of the residue from 150 ml of ether gave 4.0 g of a first crop, m.p. 82°-85° and 7.0 g of a second crop, m.p. 81°-83°
Source ID: ord-2f7ce66a3b0841688bec7cca222ca4c8Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 3-(3,4-dimethoxy-phenyl)-propylamine (12.51 g, 64.06 mmol) and TEA (10 ml, 71.84 mmol) in anhydrous THF (70 ml) was cooled to 0° C. and (3,4-dimethoxy-phenyl)-acetyl chloride (13.75 g, 64.07 mmol) in THF (28 ml) was added dropwise. After stirring at RT for 13 h under nitrogen, a saturated aqueous NaHCO3 solution was added and the reaction mixture was extracted three times with AcOEt. The organic phase was dried over anhydrous MgSO4, filtered and the solvent was removed in vacuo. A subsequent washing of the crude solid with toluene gave the title compound (12.81 g, 34.30 mmol, 53%) as a beige solid. the reaction mixture was extracted three times with AcOEt The organic phase was dried over anhydrous MgSO4 filtered the solvent was removed in vacuo A subsequent washing of the crude solid with toluene
Source ID: ord-e6e0f43bcba842739e83509c21b31b2aConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 3-(3,4-dimethoxy-phenyl)--propionamide (11.09 g, 53.00 mmol) in anhydrous THF (400 ml) was slowly added to a stirred, ice-cooled suspension of LiAlH4 (4.02 g, 106.00 mmol) in anhydrous THF (170 ml). Upon completion of the addition, the mixture was stirred at reflux for 2 h. After cooling to 0° C., H2O (5 ml) and NaOH 1N (5 ml) were added dropwise to decompose the excess of hydride. The suspension was then filtered and the residue after evaporation was partitioned between H2O (40 ml) and CH2Cl2 (100 ml). The organic layer was washed with saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, and concentrated under reduced pressure to give the crude amine (7.00 g, 35.84 mmol, 68%) as a yellow oil. cooled Upon completion of the addition at reflux for 2 h The suspension was then filtered the residue after evaporation was partitioned between H2O (40 ml) and CH2Cl2 (100 ml) The organic layer was washed with saturated aqueous NaHCO3 and brine dried over anhydrous MgSO4 concentrated under reduced pressure
Source ID: ord-872cbc1500214608914232b174f0ee3aConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a4230ea099a342c4bd4c2ef7df4cf42aConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 3-(3,4-dimethoxy-phenyl)-propionamide (11.1 g, 53.0 mmol) in anhydrous THF (400 ml) is slowly added to a stirred, ice-cooled suspension of LiAlH4 (4.02 g, 106 mmol) in anhydrous THF (170 mL). Upon completion of the addition, the mixture is stirred at reflux for 2 h. After cooling to 0° C., H2O (5 mL) and NaOH 1N (5 mL) are added dropwise to decompose the excess of hydride. The suspension is filtered and evaporated. The residue is partitioned between H2O (40 mL) and CH2Cl2 (100 mL). The organic layer is washed with saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, and concentrated under reduced pressure to give the title compound as a yellow oil. cooled Upon completion of the addition at reflux for 2 h The suspension is filtered evaporated The residue is partitioned between H2O (40 mL) and CH2Cl2 (100 mL) The organic layer is washed with saturated aqueous NaHCO3 and brine dried over anhydrous MgSO4 concentrated under reduced pressure
Source ID: ord-579fd7996d074d99b24b95d096e3a580Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 3-(3,4-dimethoxy-phenyl)-propionamide (11.1 g, 53.0 mmol) in anhydrous THF (400 ml) is slowly added to a stirred, ice-cooled suspension of LiAlH4 (4.02 g, 106 mmol) in anhydrous THF (170 mL). Upon completion of the addition, the mixture is stirred at reflux for 2 h. After cooling to 0° C., H2O (5 mL) and NaOH 1N (5 mL) are added dropwise to decompose the excess of hydride. The suspension is filtered and evaporated. The residue is partitioned between H2O (40 mL) and CH2Cl2 (100 mL). The organic layer is washed with saturated aqueous NaHCO3 and brine, dried over anhydrous MgSO4, and concentrated under reduced pressure to give the title compound as a yellow oil. cooled Upon completion of the addition at reflux for 2 h The suspension is filtered evaporated The residue is partitioned between H2O (40 mL) and CH2Cl2 (100 mL) The organic layer is washed with saturated aqueous NaHCO3 and brine dried over anhydrous MgSO4 concentrated under reduced pressure
Source ID: ord-579fd7996d074d99b24b95d096e3a580Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 0.028 mole of 3-benzoyl-2-nitrobenzeneacetic acid, 50 mL of thionyl chloride and 50 mL of benzene is heated at reflux. The dark solution is concentrated under vacuum. The residue is diluted with benzene and concentrated under vacuum (twice). A portion of the acid chloride (0.01 3 mole) in tetrahydrofuran is added to a solution of 3-amino (3,4-dimethoxyphenyl)propane (0.015 mole). The mixture is stirred at room temperature and then added to 200 mL of cold water. The resulting mixture is extracted with diethyl ether. The combined extracts are washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue is purified using standard procedures to give the product. is heated at reflux The dark solution is concentrated under vacuum The residue is diluted with benzene concentrated under vacuum (twice) The resulting mixture is extracted with diethyl ether The combined extracts are washed with water dried over sodium sulfate concentrated under reduced pressure The residue is purified to give the product
Source ID: ord-59ff462367c444bd9ff8ce202dd99d34Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 0.028 mole of 3-benzoyl-2-nitrobenzeneacetic acid, 50 mL of thionyl chloride and 50 mL of benzene is heated at reflux. The dark solution is concentrated under vacuum. The residue is diluted with benzene and concentrated under vacuum (twice). A portion of the acid chloride (0.01 3 mole) in tetrahydrofuran is added to a solution of 3-amino (3,4-dimethoxyphenyl)propane (0.015 mole). The mixture is stirred at room temperature and then added to 200 mL of cold water. The resulting mixture is extracted with diethyl ether. The combined extracts are washed with water, dried over sodium sulfate and concentrated under reduced pressure. The residue is purified using standard procedures to give the product. is heated at reflux The dark solution is concentrated under vacuum The residue is diluted with benzene concentrated under vacuum (twice) The resulting mixture is extracted with diethyl ether The combined extracts are washed with water dried over sodium sulfate concentrated under reduced pressure The residue is purified to give the product
Source ID: ord-59ff462367c444bd9ff8ce202dd99d34Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3,4-Dimethoxycinnamonitrile (5 g) was dissolved in a mixture of EtOH (100 mL) and conc. HCl (10 mL) and hydrogenated with 10% Pd/C (wet, Degussa Type E101, Aldrich) at 65 psi on a Parr shaker for 70 h. The reaction mixture was filtered over Celite and the filtrate was concentrated to remove most of the EtOH. The residue was extracted twice with Et2O (discarded) and then cooled with ice and made strongly basic with 10 M aq. NaOH solution. The basic aqueous layer was extracted with Et2O and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 3-(3,4-dimethoxyphenyl)propylamine (5.07 g) as a pale yellow oil. 1H-NMR (300 MHz, CDCl3): δ=6.68-6.78 (m, 3H), 3.83 (s, 3H, OMe), 3.82 (s, 3H, OMe), 2.70 (t, J=7.0 Hz, 2H), 2.58 (t, J=7.2 Hz, 2H), 1.70-1.75 (m, 2H), 1.17 (broad s, 2H, NH2). The reaction mixture was filtered over Celite the filtrate was concentrated to remove most of the EtOH The residue was extracted twice with Et2O (discarded) cooled with ice The basic aqueous layer was extracted with Et2O the organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure
Source ID: ord-b393c783789f4bfa9437f13e03a9d216Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 3,4-Dimethoxycinnamonitrile (5 g) was dissolved in a mixture of EtOH (100 mL) and conc. HCl (10 mL) and hydrogenated with 10% Pd/C (wet, Degussa Type E101, Aldrich) at 65 psi on a Pan shaker for 70 h. The reaction mixture was filtered over Celite and the filtrate was concentrated to remove most of the EtOH. The residue was extracted twice with Et2O (discarded) and then cooled with ice and made strongly basic with 10 M aq. NaOH solution. The basic aqueous layer was extracted with Et2O and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 3-(3,4-dimethoxyphenyl)propylamine (5.07 g) as a pale yellow oil. 1H-NMR (300 MHz, CDCl3): δ=6.68-6.78 (m, 3H), 3.83 (s, 3H, OMe), 3.82 (s, 3H, OMe), 2.70 (t, J=7.0 Hz, 2H), 2.58 (t, J=7.2 Hz, 2H), 1.70-1.75 (m, 2H), 1.17 (broad s, 2H, NH2). The reaction mixture was filtered over Celite the filtrate was concentrated to remove most of the EtOH The residue was extracted twice with Et2O (discarded) cooled with ice The basic aqueous layer was extracted with Et2O the organic layer was dried over anhydrous sodium sulfate concentrated under reduced pressure
Source ID: ord-4ee089a2a3944c64b87f7de8413f434fPubChem References
These sources are listed in the compound's public database record.
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