Triethylamine → HCID 66774573, compound

HRID 255381Notes

Reaction equation

[CH2:1]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]1[CH2:14][CH2:13][NH:12][CH:11]([CH3:15])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:31][CH2:32][OH:33].ClCCl.CO>C(#N)C>[CH2:16]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:9]1[CH2:14][CH2:13][N:12]([CH2:31][CH2:32][OH:33])[CH:11]([CH3:15])[CH2:10]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of N,N-dibenzyl-2-methylpiperidin-4-amine (Intermediate 217, 880 mg, 3.0 mmol) in acetonitrile (6 mL) was added triethylamine (0.85 ml, 6.0 mmol) and 2-bromoethanol (0.32 mL, 4.5 mmol). The reaction is stirred at 70° C. at 300 watts in the microwave for 20 minutes. Acetonitrile was removed under reduced pressure, the residue was taken up in dichloromethane (100 mL) and saturated aqueous sodium hydrogen carbonate solution (30 mL) and the aqueous phase was back extracted three times with dichloromethane (3×70 mL). The combined organic phases were dried over sodium sulfate and concentrated to dryness under reduced pressure. Chromatography of the residue on silica gel with dichloromethane/methanol (10:1) gave 660 mg (65% yield) of the product as an orange solid.

Workup

customAcetonitrile was removed under reduced pressure
extractionsaturated aqueous sodium hydrogen carbonate solution (30 mL) and the aqueous phase was back extracted three times with dichloromethane (3×70 mL)
dry with materialThe combined organic phases were dried over sodium sulfate
concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record: ord-af82a60c7ce54df18e975fcd85d0ec4e
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875715B2

Reaction notes

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