Water → HCID 131721442, compound

HRID 1602190Notes

Reaction equation

[O:1]([C:8]1[CH:25]=[CH:24][C:11]([O:12][C@@H:13]2[CH2:18][CH2:17][NH:16][CH2:15][C@H:14]2[O:19][CH2:20][CH2:21][O:22][CH3:23])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].[C:32](=[O:35])([O-:34])[O-].[K+].[K+].[OH2:38]>CN(C=O)C>[C:23]([OH:22])(=[O:38])[C:32]([OH:34])=[O:35].[CH2:27]([N:16]1[CH2:17][CH2:18][C@@H:13]([O:12][C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:25][CH:24]=2)[C@H:14]([O:19][CH2:20][CH2:21][O:22][CH3:23])[CH2:15]1)[CH2:28][CH2:29][CH2:30][CH3:31]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (±)-trans-4-(4-phenoxyphenoxy)-3-(2-methoxy-1-ethoxy)piperidine (0.50 g, 1.5 mmol) and 1-bromopentane (242 mg, 1.6 mmol) in DMF (10 ml) was added potassium carbonate (300 mg, 2.2 mmol) and the mixture was stirred at 100° C. for 3 h. Water (50 ml) was added and the product was extracted with ethyl acetate (3×20 ml). Drying over magnesium sulfate and evaporation of the solvent was followed by column chromatography on silica gel with 4% ethanol in dichloromethane. The title compound was obtained by dissolving the product in ether and adding a saturated solution of oxalic acid in ether. mp 122-124° C.

Workup

extractionthe product was extracted with ethyl acetate (3×20 ml)
dry with materialDrying over magnesium sulfate and evaporation of the solvent

Sources & evidence

ORD record: ord-88b951e0215f4f7c816119ac14dc7027
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05981539

Reaction notes

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