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CAS No. : | 1986-47-6 | MDL No. : | MFCD00063602 |
Formula : | C9H12ClN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 169.65 | Pubchem ID : | - |
Synonyms : |
SKF 385 hydrochloride;Tranylcypromine (hydrochloride);trans-2-Phenylcyclopropylamine;2-PCPA;Tranylcypromine HCl
|
Chemical Name : | trans-2-Phenylcyclopropanamine hydrochloride |
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 48.58 |
TPSA : | 26.02 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.71 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.29 |
Log Po/w (WLOGP) : | 2.3 |
Log Po/w (MLOGP) : | 2.1 |
Log Po/w (SILICOS-IT) : | 1.83 |
Consensus Log Po/w : | 1.7 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.67 |
Solubility : | 0.361 mg/ml ; 0.00213 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.47 |
Solubility : | 0.57 mg/ml ; 0.00336 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.37 |
Solubility : | 0.719 mg/ml ; 0.00424 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.69 |
Signal Word: | Danger | Class: | 6.1 |
Precautionary Statements: | P501-P270-P264-P301+P310+P330-P405 | UN#: | 2811 |
Hazard Statements: | H301 | Packing Group: | Ⅲ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With O-[(ethoxycarbonyl)cyanomethyleneamino]-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; for 24.5h; | 304 mg (0.928 mmol, 1.05 equivalents) of TOTU and 323 mul (1.857 mmol, 2.1 equivalents) of ethyldiisopropylamine were added to 0.973 mmol (1.0 equivalent) of the respective carboxylic acid in 2 ml of absolute dimethylformamide at 0C and the mixture was stirred for 20 minutes at 0C. Subsequently, 0.884 mmol (1.0 equivalent) of the respective arylcycloalkylamine hydrochloride, dissolved in 2 ml of absolute dimethylformamide, were added and the mixture was stirred for 30 minutes at 0C and for 24 h at room temperature. The reaction mixture was filtered, the filter cake washed with 20 ml of ethyl acetate and the resulting solution washed with 20 ml of 5% aqueous sodium hydrogencarbonate solution and 20 ml of 5% aqueous sodium chloride solution. The organic phase was dried over Chromabond XTR and evaporated. The obtained raw product was purified by preparative HPLC (RP-18, acetonitrile/water + 0.1 % trifluoroacetic acid). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. | |
Example 7: frans-(+/-)-Benzyl-(2-phenyl-cyclopropyl)-amine 11; [000204] To a stirred solution of trans-(+/-)-2-Phenylcyclopropylamine hydrochloride (50 mg, 0.295 mmol) in MeOH (1 ml_) were added benzaldehyde (27 uL, 0.266 mmol) and sodium cyanoborohydride (22 mg, 0.354 mmol). The mixture was stirred at 0 C for 1 h followed at room temperature overnight. To the reaction mixture was added crushed ice, and the acetonitril was removed under vacuum. The aqueous residue was extracted with CH2CI2. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative TLC using a mixture of EtOAc/Et3N (95:5) as a developing solvent to afford the title compound as a colorless oil (15.4 mg). 1H NMR (CDCI3): delta (ppm) 7.40-7.25 (m, 9 H), 7.18 (m, 1 H), 7.03 (d, 2 H, J = 7.3 Hz), 3.92 (s, 2 H), 2.42 (m, 1 H), 2.25 (m, br. s, 1 H), 1.97 (m, 1 H), 1.14 (m, 1 H), 1.01 (m, 1 H). 13C NMR (CDCI3): delta (ppm) 142.7, 140.7, 128.8 (2), 128.7 (2), 128.6 (2), 127.4, 126.3 (2), 125.9, 54.0, 41.6, 25.8, 17.5. HRMS (ESI) calculated for Ci6Hi8N+ [MH+] 224.1439; found, 224.1440. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-methyl-morpholine; In tetrahydrofuran; at -15 - 20℃; for 1.5h; | Example 3: Preparation of trans-(+/-)-Methyl-(2-phenyl-cyclopropyl)-amine; 7[000199] Acetic formic anhydride was generated by dropwise addition of formic acid (0.36 mL, 9.6 mmol) to acetic anhydride ( 0.73 ml_, 7.8 mmol) maintained on ice followed at 50 C for 2 h. The mixture was cooled to room temperature, and THF (5 mL) was added. This mixture (0.6 mL) containing acetic formic anhydride (0.3 mmol) was added to a solution of trans-(+/-)-2-phenyl-cyclopropylamine hydrochloride (50 mg, 0.3 mmol) in THF (1 mL) at -15 C followed by addition of Lambda/-methylmorpholine (45 uL, 0.3 mmol). The resulting mixture was stirred at -15 C for 30 min and at room temperature for 1 h, filtered out insoluble materials, and concentrated in vacuo. The crude residue (65 mg) was dissolved in THF (1.2 mL), and to the solution was added 1.0 M solution of borane dimethylsulfide complex in THF (0.75 mL). After the mixture was stirred at 65 C overnight, the reaction was quenched by 10% aqueous HCI. The mixture was concentrated under reduced pressure to remove THF, and the residual aqueous solution was washed with Et2theta (x1), neutralized with 10% aqueous NaOH, and then extracted with Et2O (x3). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative TLC using a mixture of EtOAc/Et3N/MeOH (8:1:1) as a developing solvent to afford the title compound as a colorless oil (21 mg). 1H NMR (CDCI3): delta (ppm) 7.30-7.25 (m, 2 H), 7.20-7.16 (m, 1 H), 7.09-7.06 (m, 2 H), 2.54 (br. s, 3 H), 2.34 (m, 1 H), 1.92 (m, 1 H), 1.76 (br. s, 1 H), 1.12-1.06 (m, 1 H), 1.02-0.98 (m, 1 H). 13C NMR (CDCI3): delta (ppm) 142.8, 128.6 (2), 126.3 (2), 125.9, 43.7, 36.2, 25.3, 17.5. HRMS (ESI) calculated for C10Hi4N+ [MH+] 148.1126; found, 148.1124. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-methyl-morpholine; In tetrahydrofuran; at -15 - 20℃; for 1.5h; | Example 4: fra/7s-(+/-)-Methyl-(2-phenyl-cyclopropylmethyl)-amine; 8[000200] Acetic formic anhydride was generated by dropwise addition of formic acid (0.18 mL, 4.8 mmol) to acetic anhydride ( 0.365 ml_, 3.9 mmol) maintained on ice followed at 50 C for 2 h. The mixture was cooled to room temperature, and THF (4.5 mL) was added. This mixture (0.53 mL) containing acetic formic anhydride (0.408 mmol) was added to a solution of trans-(+/-)-2-phenyl-cyclopropylmethylamine hydrochloride (30 mg, 0.163 mmol) in THF (1 mL) at -15 C followed by addition of Lambda/-methylmorpholine (17.9 uL, 0.163 mmol). The resulting mixture was stirred at -15 "C for 30 min and at room temperature for 1 h, filtered out insoluble materials, and concentrated in vacuo.[000201] The crude residue (42 mg) was dissolved in THF (1.2 mL), and to the solution was added 1.0 M solution of borane dimethylsulfide complex in THF (0.41 mL). After the mixture was stirred at 65 C overnight, the reaction was quenched by 10% aqueous HCI. The mixture was concentrated under reduced pressure to remove THF, and the residual aqueous solution was washed with Et2O (x1), neutralized with 10% aqueous NaOH, and then extracted with Et2O (x3). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative TLC using a mixture of EtOAc/Et.3N/MeOH (8:1:1) as a developing solvent to afford the title compound as a colorless oil (14.0 mg). 1H NMR (CDCI3):delta (ppm) 7.29-7.24 (m, 2 H), 7.18-7.15 (m, 1 H), 7.10-7.07 (m, 2 H), 2.66 (br. d, 2 H), 2.49 (br. s, 3 H), 2.37 (br. s, 1 H), 1.77 (m, 1 H), 1.38-1.32 (m, 1 H), 0.99-0.85 (m, 2 H). 13C NMR (CDCI3): delta (ppm) 143.3, 128.7, 126.2, 125.9, 56.5, 36.5, 23.3, 22.5, 15.1. HRMS (ESI) calculated for CnH16N+ [MH+] 162.1283; found, 162.1285. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-methyl-morpholine; sodium cyanoborohydride; acetic acid; In water; acetonitrile; at 20℃; for 0.666667h; | Example 5: frans-(+/-)-Dimethyl-(2-phenyl-cyclopropyl)-amine; 9[000202] To a stirred solution of fra/7s-(+/-)-2-Phenylcyclopropylamine hydrochloride (34 mg, 0.2 mmol) in acetonitrile/H2theta (1 :1 , v/v) (5 ml_) were added N- methylmorpholine (45 uL, 0.4 mmol), 37% aqueous formaldehyde (0.16 mL, 2.0 mmol), and sodium cyanoborohydride (40 mg, 0.6 mmol). Glacial acetic acid (40 uL) was added to the mixture over 10 min and the reaction was stirred at room temperature for 30 min. To the reaction mixture was added crushed ice, and the acetonitrile was removed under vacuum. The aqueous residue was extracted with CH2CI2. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative TLC using a mixture of EtOAc/Et3N (95:5) as a developing solvent to afford the title compound as a colorless oil (19.7 mg). 1H NMR (CDCI3): delta (ppm) 7.34-7.26 (m, 2 H), 7.18 (t, 1 H, J = 7.3 Hz), 7.09 (d, 2 H, J = 7.2 Hz), 2.74 (d, 2 H, J = 3.6 Hz), 2.42 (s, 6 H), 2.00 (m, 1 H), 1.83 (m, 1 H), 1.13 (m, 1 H), 0.99 (m, 1 H). 13C NMR (CDCI3): delta (ppm) 142.5, 128.6 (2), 126.5 (2), 126.0, 50.6, 45.4 (2), 25.7, 17.6. HRMS (ESI) calculated for CnH16N+ [MH+] 162.1283; found, 162.1279. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 6: Preparation of trans-(+/-)-lsopropyl-(2-phenyl-cyclopropyl)-amine 10; [000203] To a stirred solution of trans-(+/-)-2-Phenylcyclopropylamine hydrochloride (50 mg, 0.295 mmol) in MeOH (1 mL) were added acetone (21.7 uL, 0.295 mmol) and sodium cyanoborohydride (22 mg, 0.354 mmol). The mixture was stirred at 0 C for 1 h followed at room temperature overnight. To the reaction mixture was added EPO <DP n="79"/>crushed ice, and the acetonitril was removed under vacuum. The aqueous residue was extracted with CH2CI2. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative TLC using a mixture of EtOAc/Et3N (95:5) as a developing solvent to afford the title compound as a colorless oil (16.7 mg). 1H NMR (CDCI3): delta (ppm) 7.30-7.25 (m, 2 H), 7.19-7.14 (m, 1 H), 7.06 (d, 2 H, J = 7.3 Hz), 3.01 (m, 1 H), 2.31 (m, 1 H), 1.90 (m, 1 H), 1.87 (br. s, 1 H), 1.12 (d, 6 H, J = 6.3 Hz), 1.07 (m, 2 H). 13C NMR (CDCI3): delta (ppm) 142.8, 128.6 (2), 126.1 (2), 125.8, 49.7, 40.7, 25.9, 23.7, 23.6, 17.2. HRMS (ESI) calculated for Ci2H18N+ [MH+] 176.1439; found, 176.1437. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Step 2: tert-butyl 3-(cyanomethyl)-3-{4-[(trans-2-phenylcyclopropyl)amino]piperidin-1-yl}azetidine-1-carboxylate To a solution of 2-phenylcyclopropanamine hydrochloride (540 mg, 3.2 mmol, Acros: CatNo.130470050, Lot: A0295784) and tert-butyl 3-(cyanomethyl)-3-(4-oxopiperidin-1-yl)azetidine-1-carboxylate (937 mg, 3.19 mmol) in DCM (15 mL) was added acetic acid (540 muL, 9.6 mmol). The resulting yellow solution was stirred at room temperature overnight then Na(OAc)3BH (1.4 g, 6.4 mmol) was added. The reaction mixture was stirred at room temperature for 2 h then diluted with DCM and washed with saturated Na2CO3, water and brine. The organic layer was dried over Na2SO4 then concentrated. The residue was purified on a silica gel column eluting with 0 to 10% MeOH/DCM to give the desired product (1.07 g, 82%) as a yellow oil. LC-MS calculated for C24H35N4O2 (M+H)+: m/z=411.3; found 411.3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 2: (1-{4-[(trans-2-phenylcyclopropyl)amino]piperidin-1-yl}cyclobutyl)acetonitrile To a solution of 2-phenylcyclopropanamine hydrochloride (36 mg, 0.21 mmol) (trans, racemic, Acros: CatNo.130470050, Lot: A0295784) and [1-(4-oxopiperidin-1-yl)cyclobutyl]acetonitrile (41 mg, 0.21 mmol) (crude product from Step 1) in DCM (2 mL) was added acetic acid (36 muL, 0.64 mmol). The resulting yellow solution was stirred at room temperature for 2 h. Then Na(OAc)3BH (140 mg, 0.64 mmol) was added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with DCM then washed with saturated Na2CO3, water and brine. The organic layer was dried over Na2SO4 then concentrated. The residue was purified by prep. HPLC (pH=10, acetonitrile/water+NH4OH) to give the product as a white solid (trans, racemic). LC-MS calculated for C20H28N3 (M+H)+: m/z=310.2; found 310.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | Step 1: tert-butyl 3-[(trans-2-phenylcyclopropyl)amino]methyl}azetidine-1-carboxylate To a solution of tert-butyl 3-formylazetidine-1-carboxylate (556 mg, 3.00 mmol, Alfa Aesar: CatNo. H52794) and 2-phenylcyclopropanamine hydrochloride (600. mg, 3.54 mmol, trans, racemic, J&W PharmLab: CatNo.20-0073S, Lot: JW152-128A) in DCM (10 mL) was added acetic acid (510 muL, 9.0 mmol). The resulting yellow solution was stirred at room temperature overnight then Na(OAc)3BH (1.9 g, 9.0 mmol) was added. The reaction mixture was stirred at room temperature for 1 h then diluted with DCM, washed with saturated Na2CO3, water and brine. The organic layer was dried over Na2SO4 then concentrated. The residue was purified on silica gel column eluting with 0 to 100% EtOAc/Hexanes to give the desired product (513 mg, 57%) as a light yellow oil. LC-MS calculated for C14Hi9N2O2 (M-tBu+2H)+: m/z=247.1; found 247.2. | |
57% | Step 1: tert-butyl 3-[(trans-2-phenylcyclopropyl)amino]methyl}azetidine-1-carboxylate To the solution of tert-butyl 3-formylazetidine-1-carboxylate (556 mg, 3.00 mmol, Alfa Aesar: Cat No.H52794) and 2-phenylcyclopropanamine hydrochloride (600. mg, 3.54 mmol, trans, racemic, J&W PharmLab: Cat No.20-0073S, Lot: JW152-128A) in DCM (10 mL) was added acetic acid (510 muL, 9.0 mmol). The resulting yellow solution was stirred at room temperature overnight then Na(OAc)3BH (1.9 g, 9.0 mmol) was added. The reaction mixture was stirred at room temperature for 1 h then diluted with DCM, washed with saturated Na2CO3, water and brine. The organic layer was dried over Na2SO4 then concentrated. The residue was purified on silica gel column eluting with 0 to 100% EtOAc/Hexanes to give the desired product (513 mg, 57%) as a light yellow oil. LC-MS calculated for C14H19N2O2 (M-tBu+2H)+: m/z=247.1; found 247.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31.2% | To the solution of cyclohexanecarbaldehyde (59.5 mg, 0.530 mmol) in tetrahydrofuran (THF) (10 mL) and acetic acid (0.061 mL, 1.061 mmol) was added trans-2-phenylcyclopropyl]amine hydrochloride (180 mg. 1,061mmol). The reaction mixture was stirred for 1 hour, then sodium triacetoxyborohydride (450 mg, 2.122 mmol) was added and the reaction mixture stirred for 2 hours. The reaction mixture was quenched with saturated solution of NH4Cl.Water (10 mL)followed by ethyl acetate (30 mL) were added. The layers were separated and the organic layer was washed with brine, dried over MgSO4, filtered and evaporated. The oil was purified on preparative HPLC (5 to 70% AcCN: H2O gradient with 0.1% formic acid modifier). The fractions were collected. The combined fractions were neutralized with aq. NH4OH, concentrated and extracted with ethyl acetate. Organic layer was washed with brine, dried over MgSO4 and evaporated. trans-N-(Cyclohexylmethyl)-2-phenylcyclopropanamine (40 mg. 0,166 mmol. 31.2% yield) was isolated as colorless liquid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38.3% | To a stirred solution of2-(1-(pyridin-2-yl)piperidin4-ylacetaldehyde, 8 (500 mg, 2,448 mmol) in 1,2-dichloroethane (20 mL) was added acetic acid (0.420 mL, 7.34 mmol) followed by (trans)-2-phenylcyclopropanamine, hydrochloride (623 mg, 3.67 mmol) and stirred for 1 h at 25 C.Then sodiumtriacetoxyhorohydride (1556 mg, 7.34 mmol) was added and stirred for 1 h at 25 C. Reaction mixture was diluted with DCM (50 mL), washed with water (2x50 mL) and brine (1 x50 mL). The organic layer was dried over Na2S04 and concentrated under reduced pressure to afford crude product. The crude product was purified by column chromatography using 100-200 mesh silica gel by eluting with 70% ethyl acetate in petroleum ether to afford ethyl (trans)-2-phenyl-N-(2-(1-(pyridin-2-yl)piperidin-4-yl)ethyl)cyclopropanamine (400 mg, 38.3% yield) as a pale yellow solid. Isolated compound purity was less, and hence converted to the corresponding Boc-derivative for purification purpose. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | A suspension of ketone 45 (0.49 g, 2.10 mmol) and <strong>[1986-47-6](trans)-2-phenylcyclopropanamine hydrochloride</strong> (0.43 g, 2.52 mmol) in DCE (15 mL) was stirred at RT for 2.0 hrs, cooled to 0 C. then treated with the borohydride (0.80 g, 7.78 mmol). The mixture was allowed to warm to RT and stirred over 4 hrs, diluted with DCM and washed with conc. NaHCO3 solution. The organic phase was further washed with brine, dried over anhydrous Na2SO4, filtered, concentrated and purified by flash chromatography, eluent 5 then 10% MeOH in DCM (MeOH contained 2% ammonia) to form title compound 46 (0.29 g, 39% yield) as honey-like material. (0385) 1H NMR: 500 MHz, CD3OD, delta (ppm): 7.29-7.23 (m, 4H), 7.16-7.05 (m, 1H), 7.08-7.05 (m, 2H), 6.94-6.90 (m, 3H), 4.03 (t, J=6.2 Hz, 2H), 3.02 (bd, J=11.7, 2H), 2.73-2.67 (m, 1H), 2.60-2.57 (m, 2H), 2.36-2.33 (m, 1H), 2.16-2.10 (m, 2H), 2.03-1.90 (m, 5H), 1.56-1.48 (m, 2H), 1.11-1.03 (m, 2H). MS: 350.5 (calcd.), 351.1 (M+H+, found). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | A suspension of ketone 48 (0.19 g, 0.866 mmol) and <strong>[1986-47-6](trans)-2-phenylcyclopropanamine hydrochloride</strong> (0.18 g, 1.04 mmol) in DCE (10 mL) was stirred at RT for 2.0 hrs, cooled to 0 C. then treated with the borohydride (0.33 g, 1.56 mmol). The mixture was allowed to warm to RT and stirred over 4 hrs. The mixture was then diluted with DCM and washed with conc. NaHCO3 solution. The organic phase was further washed with brine, dried over anhydrous Na2SO4, filtered, concentrated and purified by flash chromatography, eluent 5 then 10% MeOH in DCM ( MeOH contained 2% ammonia) afford title compound 49 (0.19 g, 65% yield) as honey-like material. (0390) 1H NMR: 500 MHz, CD3OD, delta (ppm): 7.30-7.23 (m, 4H), 7.16-7.12 (m, 1H), 7.07-7.05 (m, 2H), 6.96-6.92 (m, 3H), 4.14 (t, J=5.7 Hz, 2H), 3.07 (bd, J=12.2, 2H), 2.83 (t, J=5.6 Hz, 2H), 2.73-2.67 (m, 1H), 2.36-2.33 (m, 1H), 2.27-2.19 (m, 2H), 2.01-1.90 (m, 3H), 1.58-1.50 (m, 2H), 1.11-1.03 (m, 2H). MS: 336.5 (calcd.), 337.1 (M+H+, found). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
7% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound. |
Tags: 1986-47-6 synthesis path| 1986-47-6 SDS| 1986-47-6 COA| 1986-47-6 purity| 1986-47-6 application| 1986-47-6 NMR| 1986-47-6 COA| 1986-47-6 structure
A789635[ 155-09-9 ]
trans-2-Phenylcyclopropanamine
Reason: Free-Salt
[ 6604-06-4 ]
rel-(1R,2S)-2-Phenylcyclopentan-1-amine
Similarity: 0.91
[ 20388-87-8 ]
2-Phenylpropan-1-amine hydrochloride
Similarity: 0.87
[ 6604-06-4 ]
rel-(1R,2S)-2-Phenylcyclopentan-1-amine
Similarity: 0.91
[ 20388-87-8 ]
2-Phenylpropan-1-amine hydrochloride
Similarity: 0.87
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H412 | Harmful to aquatic life with long-lasting effects |
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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