Dimethylamine → HCID 53321082, compound

HRID 333269Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:8]2([CH:14]=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH3:16][NH:17][CH3:18]>>[F:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:14][N:17]([CH3:18])[CH3:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 674Dimethylamine

HCID 58954784HCID 58954784, compound

Product 1

HCID 53321082HCID 53321082, compoundYield 39.1%

Procedure

The title compound was prepared from 1-(3-fluorophenyl)cyclohexane-carbaldehyde (103 mg, 0.50 mmol) and dimethylamine (2.0 M in THF, 2.5 ml, 5.0 mmol) according to General Procedure H2.The crude product was purified by column chromatography (SiO2, MeOH/CH2Cl2, MeOH from 0% to 15%) to give 1-(1-(3-fluorophenyl)cyclohexyl)-N,N-dimethylmethanamine (46 mg, 39%) as a clear oil. 1H NMR (CDCl3): δ 1.32-1.38 (m 3H), 1.49-1.56 (m, 3H), 1.59-1.66 (m, 2H), 1.99 (s, 6H), 2.05-2.09 (m, 2H), 2.33 (s, 2H), 6.83-6.88 (m, 1H), 7.08 (d, J=8.0 Hz, 1H), 7.14 (d, J=8.0 Hz, 1H), 7.23-7.29 (m, 1H). 13C NMR (CDCl3) δ 22.4, 26.8, 34.4, 43.6, 48.6, 72.9, 112.2, 112.4, 114.6, 114.8, 123.2, 129.4, 129.5, 162.0, 164.5.ESI MS m/z 236.

Workup

customThe crude product was purified by column chromatography (SiO2, MeOH/CH2Cl2, MeOH from 0% to 15%)

Sources & evidence

ORD record: ord-3d923ad4d60a40059a93062c193441df
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877975B2

Reaction notes

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