Ammonium Chloride → HCID 13882441, compound

HRID 1583320Notes

Reaction equation

[CH2:1]([Li])[CH3:2].[CH3:4][O:5][C:6]1[CH:31]=[CH:30][CH:29]=[CH:28][C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]2[CH2:26][CH3:27])=[CH:12][CH:11]=1)=[O:9].[Cl-].[NH4+]>O1CCCC1>[CH2:26]([CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25][N:20]1[CH2:19][CH2:18][CH2:17][O:16][C:13]1[CH:12]=[CH:11][C:10]([C:8]([C:7]2[CH:28]=[CH:29][CH:30]=[CH:31][C:6]=2[O:5][CH3:4])([OH:9])[CH2:1][CH3:2])=[CH:15][CH:14]=1)[CH3:27]

Participants

Conditions

Temperature: -15 °C

Procedure

To 125 ml. of a 0.8 molar ethereal ethyl lithium solution a solution of 15.3 g. of 2-methoxy-4'-[3-(2-ethyl-piperid-1-yl)-propoxy]-benzophenone in 50 ml. of tetrahydrofuran is added dropwise, in argon atmosphere, with stirring at -15° C. The reaction mixture is stirred at room temperature for another two hours, whereupon it is decomposed with a saturated aqueous ammonium chloride solution under cooling. The aqueous phase is extracted with ether. The combined organic phases are washed with a saturated aqueous sodium chloride solution, and dried over anhydrous potassium carbonate. The solvent is distilled off under reduced pressure, and the residue is fractionated. 7.6 g. of the title compound are obtained. The physical characteristics of the product are identical with those given in Example 1.

Workup

stirringThe reaction mixture is stirred at room temperature for another two hours, whereupon it
temperatureunder cooling
extractionThe aqueous phase is extracted with ether
washThe combined organic phases are washed with a saturated aqueous sodium chloride solution
dry with materialdried over anhydrous potassium carbonate
distillationThe solvent is distilled off under reduced pressure

Sources & evidence

ORD record: ord-98ecc926f87747bb9eb7b5f7ceabd248
Source dataset: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04551465

Reaction notes

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