Formic Acid → 4-(4-Bromo-7-methoxybenzofuran-2-ylmethoxy)-1-methyl-piperidine

HRID 1108321Notes

Reaction equation

[Br:1][C:2]1[C:7]2[CH:8]=[C:9]([CH2:11][O:12][CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[O:10][C:6]=2[C:5]([O:19][CH3:20])=[CH:4][CH:3]=1.[CH:21](O)=O.C=O.[OH-].[Na+]>O>[Br:1][C:2]1[C:7]2[CH:8]=[C:9]([CH2:11][O:12][CH:13]3[CH2:18][CH2:17][N:16]([CH3:21])[CH2:15][CH2:14]3)[O:10][C:6]=2[C:5]([O:19][CH3:20])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 95 °C

Procedure

4-(4-Bromo-7-methoxybenzofuran-2-ylmethoxy)-piperidine (0.98 g), formic acid (0.65 ml) and formaldehyde (0.56 g of a 37% w/w solution in water) were combined and heated to 95° C. overnight. After cooling to room temperature the mixture was diluted with water (70 ml) and a concentrated aqueous solution of sodium hydroxide added until the solution was basic (pH=14). It was extracted with ethyl acetate (2×100 ml). The combined organic extracts were dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a pale yellow oil (1.03 g).

Workup

temperatureAfter cooling to room temperature the mixture
extractionIt was extracted with ethyl acetate (2×100 ml)
dry with materialThe combined organic extracts were dried over magnesium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-2c30f4d6f10b403da90778f12af7fde8
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06066657

Reaction notes

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