Water → 3-(1H-indol-1-yl)-N-methyl-3-phenylpropan-1-amine

HRID 250194Notes

Reaction equation

[Na+].[I-].Cl[CH2:4][CH2:5][CH:6]([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O.[CH3:23][NH2:24]>>[N:13]1([CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4][NH:24][CH3:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1

Participants

Reactant 4

HCID 962Water

HCID 5238Sodium Iodide

HCID 6329Methylamine

HCID 580884211-(3-chloro-1-phenyl-propyl)-1H-indole

Product 1

HCID 445934393-(1H-indol-1-yl)-N-methyl-3-phenylpropan-1-amineYield 90%

Conditions

Temperature: 100 °C

Procedure

A suspension of NaI (0.235 g, 1.56 mmol) and 1-(3-chloro-1-phenyl-propyl)-1H-indole (0.141 mg, 0.52 mmol) in ethanolic methylamine solution (33%, 2 mL) was heated at 100° C. for 1 hour under microwave irradiation (sealed tube). The reaction mixture was poured into water (30 mL) and extracted with CH2Cl2 (3×25 mL). The combined organic layers were dried (Na2SO4), and evaporated under vacuum. Purification by chromatography (SiO2, CH2Cl2-MeOH—NH4OH, 18:1:0.1) gave 0.125 g (90% yield) of pure (3-indol-1-yl-3-phenyl-propyl)-methyl-amine as an oil. Treatment of this amino compound with an ethereal solution of HCl (2M, 0.26 mL) gave the corresponding hydrochloride salt (0.127 g) as a white powder: mp=218-219° C.; 1H NMR (DMSO) δ 2.53 (s, 3H), 2.60-2.89 (m, 4H), 5.86-5.91 (m, 1H), 6.585 (d, 1H, J=3.22 Hz), 6.98-7.12 (m, 2H), 7.20-7.34 (m, 5H), 7.52-7.54 (m, 2H), 7.71 (d, 1H, J=3.22 Hz), 9.0 (broad s, 1H); MS (EI) m/z 265 (M+H)+.

Workup

extractionextracted with CH2Cl2 (3×25 mL)
dry with materialThe combined organic layers were dried (Na2SO4)
customevaporated under vacuum
customPurification by chromatography (SiO2, CH2Cl2-MeOH—NH4OH, 18:1:0.1)

Sources & evidence

ORD record: ord-cbc4b327a7eb44d296f3f5505c52c630
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863305B2

Reaction notes

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