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

HRID 1743202
Notes
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Reaction equation

HRID 1743202 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 222382813-(4-Isopropylphenyl)-4,6,7-trimethylspiro[benzofuran-2(3H),4'-piperidine]-5-ol Hydrochloride

Product 1

HCID 222382593-(4-Isopropylphenyl)-1',4,6,7-tetramethylspiro[benzofuran-2(3H), 4'-piperidine]-5-olYield 77%

Reagents, catalysts & solvents 1

HCID 284
Formic Acid
Solvent

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

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted twice with ethyl acetate
  3. washwashed with an aqueous saturated sodium hydrogencarbonate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes