4-[3-(1H-indol-3-yl)propylidene]-1-butyl-N,N-dimethylcyclohexanamine → N,N-dimethyl-N-(4-butyl-2',3',4',9'-tetrahydro-1H-spiro[cyclohexane-1,1'-carbazole]-4-yl)amine

HRID 2064525Notes

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH:12]=[C:13]2[CH2:18][CH2:17][C:16]([CH2:22][CH2:23][CH2:24][CH3:25])([N:19]([CH3:21])[CH3:20])[CH2:15][CH2:14]2)=[CH:2]1>C1(C)C=CC=CC=1.ClCCl>[CH3:20][N:19]([CH3:21])[C:16]1([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:17][CH2:18][C:13]2([C:2]3[NH:1][C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[C:3]=3[CH2:10][CH2:11][CH2:12]2)[CH2:14][CH2:15]1

Participants

Conditions

Temperature: 100 °C

Procedure

p-toluol sulphonic acid (323 mg, 1.7 mmol) was added to a solution 4-[3-(1H-indol-3-yl)propylidene]-1-butyl-N,N-dimethylcyclohexanamine (289 mg, 0.85 mmol) in absolute toluol (10 mL) and stirred for 18 h at 100° C. The reaction solution was then diluted with dichloromethane (30 mL) and washed with 1 N sodium carbonate solution (2×30 mL), water and saturated sodium chloride solution (30 mL each) one after the other, dried with sodium sulphate and concentrated to low volume in a vacuum. The raw product (272 mg) was mixed with methanol (100 mL) and stirred overnight at room temperature, during which very little precipitate was formed (light-coloured solid). The 1H-NMR spectrum and the LC-MS data showed that this concerned two isomers, and the 1H-NMR spectrum revealed that these were present in a ratio of approx. 1:1 and olefin side-products were present at most in very small quantity. The reaction solution was concentrated to low volume in a vacuum (259 mg, 90%). The diastereomer mixture was separated by preparative HPLC.

Workup

washwashed with 1 N sodium carbonate solution (2×30 mL), water and saturated sodium chloride solution (30 mL each) one after the other,
dry with materialdried with sodium sulphate
concentrationconcentrated to low volume in a vacuum
additionThe raw product (272 mg) was mixed with methanol (100 mL)
stirringstirred overnight at room temperature, during which very little precipitate
customwas formed (light-coloured solid)
concentrationThe reaction solution was concentrated to low volume in a vacuum (259 mg, 90%)
customThe diastereomer mixture was separated by preparative HPLC

Sources & evidence

ORD record: ord-71ae13e89f7a4649b21a23e959b1f8f7
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288430B2

Reaction notes

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