Dimethylamine → HCID 58954887, compound

HRID 333262Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH:16]=O)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[CH3:18][NH:19][CH3:20]>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH2:16][N:19]([CH3:20])[CH3:18])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

Reactant 2

HCID 674Dimethylamine

HCID 58954806HCID 58954806, compound

Product 1

HCID 58954887HCID 58954887, compoundYield 33%

Procedure

The title compound was prepared from the above 1-(benzo[d][1,3]dioxol-5-yl)cyclohexanecarbaldehyde (232 mg, 1.0 mmol) and dimethylamine (2.0 M in THF, 1.0 ml, 2.0 mmol) according to General Procedure H2.The crude product was purified by silica gel column chromatography (MeOH/CH2Cl2, MeOH from 0% to 15%) to give 1-(1-(benzo[d][1,3]dioxol-5-yl)cyclohexyl)-N,N-dimethylmethanamine (47 mg, 33%) as clear oil. 1H NMR (CDCl3): δ 1.31-1.41 (m 3H), 1.42-1.53 (m, 3H), 1.56-1.63 (m, 2H), 2.01 (s, 6H), 2.03-2.08 (m, 2H), 2.30 (s, 2H), 5.91 (s, 2H), 6.75 (d, J=8.0 Hz, 1H), 6.82 (dd, J=8.0 Hz, 1.6 Hz, 1H), 6.87 (d, J=1.6 Hz, 1H). 13C NMR (CDCl3) δ 22.4, 26.8, 34.7, 37.5, 43.2, 48.2, 73.0, 100.9, 108.0, 108.2, 120.5, 140.3, 145.3, 147.8.ESI MS m/z 262.

Workup

customThe crude product was purified by silica gel column chromatography (MeOH/CH2Cl2, MeOH from 0% to 15%)

Sources & evidence

ORD record: ord-42841c2eb65d421698eedc36c3cc3737
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877975B2

Reaction notes

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