Ammonium Chloride → 2-Fluoro-9-(1-methylpiperidin-4-YL)-9H-xanthen-9-OL

HRID 2083754Notes

Reaction equation

HRID 2083754 reaction equation
[Mg].Cl[CH:3]1[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1.[F:10][C:11]1[CH:24]=[CH:23][C:22]2[O:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14](=[O:25])[C:13]=2[CH:12]=1.[Cl-].[NH4+]>>[F:10][C:11]1[CH:24]=[CH:23][C:22]2[O:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH:3]3[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]3)([OH:25])[C:13]=2[CH:12]=1

Participants

5

Reactant 4

HCID 25517Ammonium ChlorideHCID 793424-chloro-N-methylpiperidineHCID 5462224MagnesiumHCID 116009562-Fluoro-9H-xanthen-9-one

Product 1

HCID 203575052-Fluoro-9-(1-methylpiperidin-4-YL)-9H-xanthen-9-OL

Procedure

The Grignard reagent prepared from 0.53 g. (0.0216 m.) of magnesium and 2.9 g. (0.0216 m.) of 4-chloro-N-methylpiperidine is reacted with 2.3 g. (0.0108 m.) of 2-fluoroxanthone as described in Example 3. The reaction mixture is heated for four hours and then decomposed with saturated ammonium chloride solution to yield 2-fluoro-9-(1-methyl-4-piperidyl)-xanthene-9-ol, m.p. 193°-200° C.

Workup

  1. temperatureThe reaction mixture is heated for four hours

Sources & evidence

ORD record
ord-cc9d9e696613425293869ce30d789a4d
Source dataset
uspto-grants-1978_04
Patent number
US04086350

Reaction notes

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