Reaction SMILES: Cl.[NH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1.[CH2:14]([O:16][C:17](=[O:20])[CH:18]=O)[CH3:15]>C(O)C.C1(C)C=CC=CC=1>[CH2:14]([O:16][C:17]([C:18]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH:4]=[CH:3][N:2]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3)=[O:20])[CH3:15]
Reactant: NCCc1c[nH]c2ccccc12
Reactant: CCOC(=O)C=O
Agent: Cl
Solvent: CCO
Solvent: Cc1ccccc1
Product: CCOC(=O)c1nccc2c1[nH]c1ccccc12
Temperature: 25 °C
Reaction time: 8 h
Yield: 51.6 %

Procedure:
To a suspension of tryptamine hydrochloride (2.00 g, 10.17 mmol) in ethanol (25 mL) was added a solution of glyoxylic acid ethyl ester (3.12 g, 15.26 mmol) in toluene (50% v/v) at 0° C. After the reaction mixture was stirred overnight at ambient temperature, the solvent was removed under reduced pressure. The resulting residue was treated with saturated aqueous sodium bicarbonate. The product was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude product was used in the next step without further purification. Step b: To a solution of the resulting crude residue in o-xylene (20 mL) at 0° C. was added 10% Pd/C (0.51 g). The mixture was stirred overnight at 140° C. under an air atmosphere. The reaction mixture was filtered through Celite, washed with chloroform and concentrated. The resulting residue was purified by chromatography on silica gel (0-20% ethyl acetate/hexanes) to afford 1.26 g (52% yield) of product 1: 1H NMR (400 MHz, CDCl3) δ 9.92 (bs, 1H), 8.59 (d, J=4.8 Hz, 1H), 8.16-8.13 (m, 2H), 7.62-7.55 (m, 2H), 7.32 (dt, J=1.2, 7.0 Hz, 1H), 4.59 (q, J=7.2 Hz, 2H), 1.53 (t, J=7.2 Hz, 3H); ESI+ MS: m/z (rel intensity) 241.1 (100, [M+H]+). Step c: Preparation of 9H-pyrido[3,4-b]indole-1-carbaldehyde (2). To a stirred solution of ethyl-9H-pyrido[3,4-b]indole-1-carboxylate, 1, (1.26 g, 5.24 mmol) in CH2Cl2 (50 mL) was added a DIBAL-H solution (1.0 M in toluene; 36.0 mL, 36.71 mmol) at −50° C. The mixture was stirred at −50° C. for 10 min and quenched by sequential addition of methanol (14.0 mL) and 10% NaOH (10 mL) at −50° C. Then the mixture was stirred at ambient temperature for an additional 1 h. The precipitates were removed by filtration through Celite and washed with CHCl3-methanol (10:1). The combined filtrates were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The product was purified by chromatography on silica gel (2-20% methanol/CH2Cl2) to afford 0.46 g (45% yield) of β-carboline-1-carbaldehyde, 2: 1H NMR (400 MHz, CDCl3) δ 10.33 (s, 1H), 10.04 (bs, 1H), 8.63 (d, J=5.2 Hz, 1H), 8.18-8.15 (m, 2H), 7.64-7.57 (m, 2H), 7.35 (dt, J=1.6, 7.6 Hz, 1H); ESI+ MS: m/z (rel intensity) 197.0 (100, [M+H]+). Steps d and e: Preparation of tert-butyl 4-(5,6,7,8-tetrahydroquinolin-8-ylamino)butylcarbamate (3). To a solution of 6,7-dihydroquinolin-8(5H)-one (2.0 g, 13.6 mmol) in ethanol (15 mL) was added concentrated acetic acid (5 drops), tert-butyl 4-aminobutylcarbamate (2.7 g, 14.3 mmol) and 4 Å molecular sieves. The reaction mixture was heated at 150° C. in microwave reactor for 10 min. The mixture was cooled to room temperature and NaBH4 (0.8 g, 20.4 mmol) was added all at once. The crude reaction mixture was absorbed onto silica gel and the product purified by silica gel chromatography (0% to 10% methanol/CH2Cl2) to afford the desired product: ESI+ MS: m/z (rel intensity) 320.2 (100, [M+H]+) Step f: Preparation of tert-butyl 4-(((9H-pyrido[3,4-b]indol-1-yl)methyl)(5,6,7,8-tetrahydroquinolin-8-yl)amino)butylcarbamate (4). A heavy-walled Pyrex tube was charged with a solution of 9H-pyrido[3,4-b]indole-1-carbaldehyde, 2, (0.20 g, 1.02 mmol) in 1,2-dichloroethane (5 mL). This solution was treated with tert-butyl 4-(5,6,7,8-tetrahydroquinolin-8-ylamino)butylcarbamate, 3, (0.36 g, 1.12 mmol), sodium triacetoxyborohydride (0.43 g, 2.04 mmol), 4A molecular sieves and a catalytic amount of acetic acid (2 drops). The reaction mixture was exposed to microwave irradiation for 10 min at a temperature of 100° C. After the irradiation, the reaction mixture was cooled with high-pressure air until the temperature had fallen below 40° C. The crude reaction mixture was poured onto a saturated aqueous solution of sodium bicarbonate. The product was extracted with dichloromethane. The combined organic layers were washed with brine, dried over potassium carbonate, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (0-5% methanol/CH2Cl2) to afford 0.12 g (24% yield) of desired product 4: 1H NMR (400 MHz, CDCl3) δ 13.43 (bs, 1H), 8.67 (d, J=3.6 Hz, 1H), 8.24 (d, J=5.6 Hz, 1H), 8.10 (d, J=7.6 Hz, 1H), 7.82 (d, J=5.2 Hz, 1H), 7.69 (d, J=8.4 Hz, 1H), 7.54 (dt, J=1.2, 7.4 Hz, 1H), 7.41 (d, J=7.2 Hz, 1H), 7.21 (dt, J=0.8, 7.2 Hz, 1H), 7.14 (dd, J=4.8, 7.6 Hz, 1H), 4.28-4.02 (m, 4H), 2.90-2.60 (m, 5H), 2.44-2.26 (m, 2H), 2.12-2.04 (m, 1H), 1.96-1.84 (m, 1H), 1.80-1.65 (m, 1H), 1.44-1.25 (m, 1H), 1.33 (s, 9H), 1.22-1.12 (m, 1H); ESI+ MS: m/z (rel intensity) 500.2 (100, [M+H]+). Step g: Preparation of N-((9H-pyrido[3,4-b]indol-1-yl)methyl)-N-(4-aminobutyl)-5,6,7,8-tetrahydroquinolin-8-amine tetrahydrochloride (A). A solution of tert-butyl 4-(((9H-pyrido[3,4-b]indol-1-yl)methyl)(5,6,7,8-tetrahydroquinolin-8-yl)amino)-butylcarbamate, 4, (0.12 g, 0.24 mmol) in methanol (5 mL) was treated with thionyl chloride (1 mL) at room temperature. The resulting mixture was stirred for 30 min. The reaction mixture was then concentrated and dried under reduced pressure to afford 0.11 g (80% yield) of the desired product A: 1H NMR (400 MHz, d6-DMSO) δ 13.49 (bs, 1H), 8.80-8.41 (m, 3H), 8.00-7.82 (m, 3H), 7.80 (d, J=8.0 Hz, 1H), 7.78-7.70 (m, 1H), 7.39 (t, J=7.2 Hz, 1H), 4.95-4.85 (m, 1H), 4.68-4.50 (m, 2H), 2.98-2.82 (m, 2H), 2.61-2.50 (m, 2H), 2.47-2.35 (m, 3H), 2.12-1.94 (m, 2H), 1.80-1.30 (m, 5H); ESI+ MS: m/z (rel intensity) 400.2 (100, [M+H]+).