Formic Acid → HCID 21108118, compound

HRID 1766022Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14](=[O:30])[CH2:15][CH2:16][C:17]([C:19]3[CH:29]=[CH:28][C:22]4[CH2:23][CH2:24][NH:25][CH2:26][CH2:27][C:21]=4[CH:20]=3)=[O:18])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C=O.[CH:33](O)=O.[OH-].[Na+]>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][N:11]([C:14](=[O:30])[CH2:15][CH2:16][C:17]([C:19]3[CH:29]=[CH:28][C:22]4[CH2:23][CH2:24][N:25]([CH3:33])[CH2:26][CH2:27][C:21]=4[CH:20]=3)=[O:18])[CH2:12][CH2:13]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-[4-(4-chlorophenyl)-1-piperidinyl]-4-oxo-1-(2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-1-butanone (0.3 g, 0.70 mmol) obtained in Example 15, formaldehyde (0.086 ml, 1.06 mmol) and formic acid (0.9 ml) was heated at 100° C. for 4 hours, then poured into water, made basic with 8 N aqueous sodium hydroxide and extracted with ethyl acetate. The extract was washed with water and then with a saturated saline solution, and dried over anhydrous magnesium sulfate. After the solvent was distilled away under reduced pressure, the residues were purified by alumina column chromatography (developing solvent; ethyl acetate-methanol=10:1), whereby 0.15 g of the title compound was obtained as colorless powder.

Workup

extractionextracted with ethyl acetate
washThe extract was washed with water
dry with materialwith a saturated saline solution, and dried over anhydrous magnesium sulfate
distillationAfter the solvent was distilled away under reduced pressure
customthe residues were purified by alumina column chromatography (developing solvent; ethyl acetate-methanol=10:1)

Sources & evidence

ORD record: ord-5978731beaed493eb5715e8c6d833cf7
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07229986B2

Reaction notes

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