Formaldehyde → 3-Chloro-4-(1-methylpiperidin-4-yloxy)nitrobenzene

HRID 1796197Notes

Reaction equation

C(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=2[Cl:24])[CH2:10][CH2:9]1)=O)(C)(C)C.C=O.C(=O)([O-])[O-].[K+].[K+]>C(O)=O>[Cl:24][C:16]1[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:15]=1[O:14][CH:11]1[CH2:12][CH2:13][N:8]([CH3:6])[CH2:9][CH2:10]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 4-(1-t-butoxycarbonylpiperidin-4-yloxy)-3-chloronitrobenzene (1.50 g) obtained in reference example 3 in 90% formic acid (4.00 g) was added 37% formaldehyde (2.50 g), and the resulting mixture was stirred at 100° C. for 2 hours. After cooling to room temperature, the reaction mixture was neutralized with an aqueous potassium carbonate solution and extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated in vacuo to afford the title compound (1.12 g, yield: 98%) as a yellow solid.

Workup

temperatureAfter cooling to room temperature
extractionextracted with ethyl acetate
washThe extract was washed with a saturated aqueous sodium chloride solution
dry with materialdried over anhydrous magnesium sulfate
customevaporated in vacuo

Sources & evidence

ORD record: ord-c91b2367e7bb48f3abd0c7a0c627397f
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030138B2

Reaction notes

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