Methylamine → HCID 58954911, compound

HRID 333263Notes

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][NH2:19]>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3([CH2:16][NH:19][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 6329Methylamine

HCID 58954806HCID 58954806, compound

Product 1

HCID 58954911HCID 58954911, compoundYield 88.1%

Procedure

The title compound was prepared from 1-(benzo[d][1,3]dioxol-5-yl)cyclohexanecarbaldehyde (232 mg, 1.0 mmol) and methylamine (2.0 M in THF, 3 ml, 6.0 mmol) according to General Procedure H2.The crude product was purified by silica gel column chromatography (SiO2, MeOH/CH2Cl2, MeOH from 0% to 20%) to give 1-(1-(benzo[d][1,3]dioxol-5-yl)cyclohexyl)-N-methylmethanamine (218 mg, 88%). 1H NMR (CDCl3): δ 1.26-1.52 (m 4H), 1.54-1.61 (m, 2H), 1.66-1.73 (m, 2H), 2.03-2.12 (m, 2H), 2.28 (s, 3H), 2.60 (s, 2H), 5.90 (s, 2H), 6.75-6.86 (m, 2H), 6.90 (s, 1H). 13C NMR (CDCl3) δ 22.3, 26.7, 35.2, 37.4, 42.3, 64.8, 101.0, 107.6, 108.2, 120.3, 139.4, 145.6, 148.1.ESI MS m/z 248.

Workup

customThe crude product was purified by silica gel column chromatography (SiO2, MeOH/CH2Cl2, MeOH from 0% to 20%)

Sources & evidence

ORD record: ord-9864413cc8cd47bda8ba7e41409599ec
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877975B2

Reaction notes

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