Formaldehyde → HCID 25052431, compound

HRID 1785342Notes

Reaction equation

[CH2:1]=O.Cl.[CH3:4][N:5]([CH3:28])[C:6](=[O:27])[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([NH:25][CH3:26])[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH:9]=1.[OH-].[Na+]>C(O)=O>[CH3:28][N:5]([CH3:4])[C:6](=[O:27])[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([N:25]([CH3:1])[CH3:26])[CH2:15][CH2:16][C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[CH:9]=1

Participants

Conditions

Temperature: 90 °C

Procedure

Formic acid (10 ml) and 35% aqueous formaldehyde solution (10 ml) were added to 3-[3-(4-methoxyphenyl)-1-methylaminopropyl]phenyl dimethylcarbamate (500 mg, 1.4 mmol) obtained from Example 2 and the mixture was stirred at 90° C. for 2 hours. After cooling the reaction mixture to room temperature the mixture was neutralized with 1N aqueous sodium hydroxide solution. The neutralized mixture was extracted with ether and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate:methanol=80:20 as the eluent to give 3-[1-dimethylamino-3-(4-methoxyphenyl)propyl]phenyl dimethylcarbamate. The product was treated with 1N hydrogen chloride/ethyl acetate solution to afford the title compound as an amorphous solid.

Workup

temperatureAfter cooling the reaction mixture to room temperature the mixture
extractionThe neutralized mixture was extracted with ether
dry with materialthe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record: ord-1b256bb1e6434c5aa777f586588f7455
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504437B2

Reaction notes

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