Formaldehyde → 5-methoxy-3-(N-methyl-piperidin-3-ylmethyl)-1H-indole

HRID 356001Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][NH:15][CH2:14]1.[CH2:19]=O.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][N:15]([CH3:19])[CH2:14]1

Participants

Conditions

Temperature: 10 °C

Procedure

To a stirred solution of compound of Description 6 [5-methoxy-3-(piperidin-3-ylmethyl)-1H-indole] (2 g, 0.0082 mol) in methanol (50 ml) was added dropwise aqueous formaldehyde (40%) (5.63 ml; 0.082 mol). The mixture was heated at reflux for 2 hours. The reaction mixture was cooled at 10° C. and then sodium borohydride (0.93 g; 0.025 mol) was added. The resulting mixture was stirred at room temperature for 1.5 hours. The reaction was then quenched with water and the solvent (methanol) was evaporated under vacuum. The product was extracted with ethyl acetate, the organic extract was dried (Mg SO4) and evaporated under vacuum, then the compound was triturated with diethyl ether and dried under vacuum giving the title compound as a solid (1.8 g)

Workup

temperatureThe mixture was heated
temperatureat reflux for 2 hours
customThe reaction was then quenched with water
customthe solvent (methanol) was evaporated under vacuum
extractionThe product was extracted with ethyl acetate
extractionthe organic extract
dry with materialwas dried (Mg SO4)
customevaporated under vacuum
customthe compound was triturated with diethyl ether
customdried under vacuum

Sources & evidence

ORD record: ord-ba8fec9e785e4dfc997335ad2c4df577
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05834493

Reaction notes

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