Triethylamine → 1-{[trans-4-(2,4-Dichlorophenyl)-5-nitrocyclohex-1-en-1-yl]methyl}piperidin-4-ol

HRID 1172337Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:8]1[C@H:13]([N+:14]([O-:16])=[O:15])[CH2:12][CH:11]=[CH:10][CH2:9]1.CS([Cl:21])(=O)=O.[CH2:22]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])C.N1CC[CH:32]([OH:35])CC1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:21])[CH:5]=[CH:4][C:3]=1[C@H:8]1[C@H:13]([N+:14]([O-:16])=[O:15])[CH2:12][C:11]([CH2:22][N:24]2[CH2:27][CH2:28][CH:32]([OH:35])[CH2:26][CH2:25]2)=[CH:10][CH2:9]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold (0° C.) CH2Cl2 (1 mL) solution of Example 1A (61 mg, 0.2 mmol), methanesulfonyl chloride (0.017 mL, 0.22 mmol) and triethylamine (0.035 mL, 0.25 mmol) were added. After it was stirred at 0° C. for five minutes, more triethylamine (0.035 mL, 0.25 mmol) and piperidin-4-ol (25 mg, 0.24 mmol) were added to the reaction mixture. The reaction was allowed to warm from 0° C. to room temperature overnight. It was diluted with CH2Cl2, washed with water and brine, dried over sodium sulfate, filtered, concentrated under reduced pressure and purified by high pressure liquid chromatography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid) to provide the title compound (54 mg, 69%). MS (DCI) m/z 386 (M+H)+.

Workup

temperatureto warm from 0° C. to room temperature overnight
washwashed with water and brine
dry with materialdried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
custompurified by high pressure liquid chromatography (eluting with 0-70% acetonitrile/water and 0.1% trifluoroacetic acid)

Sources & evidence

ORD record: ord-ced110350a19409e837d9918ca383962
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834012B2

Reaction notes

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