Formaldehyde → 3-(4-Isopropylphenyl)-1',4,6,7-tetramethylspiro[benzofuran-2(3H), 4'-piperidine]-5-ol

HRID 1743202Notes

Reaction equation

Cl.[CH:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[C:15]3([CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[O:14][C:13]3[C:21]([CH3:28])=[C:22]([CH3:27])[C:23]([OH:26])=[C:24]([CH3:25])[C:12]2=3)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[CH2:29]=O.[OH-].[Na+]>C(O)=O>[CH:2]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[C:15]3([CH2:16][CH2:17][N:18]([CH3:29])[CH2:19][CH2:20]3)[O:14][C:13]3[C:21]([CH3:28])=[C:22]([CH3:27])[C:23]([OH:26])=[C:24]([CH3:25])[C:12]2=3)=[CH:9][CH:10]=1)([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3-(4-isopropylphenyl)-4,6,7-trimethylspiro[benzofuran-2(3H),4′-piperidine]-5-ol hydrochloride (2.80 g, 6.97 mmol), formic acid (30 mL) and 37% formalin (30 mL) was stirred for 15 hours at 100° C. The reaction mixture was cooled to room temperature, made basic with 8N sodium hydroxide solution, and extracted twice with ethyl acetate. The organic layers were combined, washed with an aqueous saturated sodium hydrogencarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (Chromatorex NH DM1020, Fuji Silysia Chemical LTD) (hexane/ethyl acetate=1/1) to obtain the title compound (2.05 g, yield 77%).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted twice with ethyl acetate
washwashed with an aqueous saturated sodium hydrogencarbonate
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-82959380b84a4efdbbd1dae7ba4f0bef
Source dataset: uspto-grants-2006_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07008950B1

Reaction notes

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