Water → 1-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)piperidine-3-carboxylic acid ethyl ester

HRID 2365981Notes

Reaction equation

HRID 2365981 reaction equation
Br[CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1.[NH:13]1[CH2:23][CH2:22][CH2:21][CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14]1.CCN(C(C)C)C(C)C.O>CN(C=O)C>[CH2:19]([O:18][C:16]([CH:15]1[CH2:21][CH2:22][CH2:23][N:13]([CH2:2][CH:3]2[O:8][C:7]3[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=3[O:5][CH2:4]2)[CH2:14]1)=[O:17])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 983332-Bromomethyl-1,4-benzodioxaneHCID 98969Ethyl nipecotate

Product 1

HCID 251754981-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)piperidine-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2-bromomethyl-2,3-dihydrobenzo[1,4]dioxine (3.0 g, 13.09 mmol) and ethyl nipecotate (2.65 ml, 17.02 mmol) in DMF (15 ml) was added DIPEA (7.5 ml). The reaction mixture was irradiated in the microwave reactor at 110° C. for 3 min. Water (20 ml) was then added. The reaction mixture was extracted with DCM (3×20 ml). The combined organic phases were dried over Na2SO4, filtered and evaporated to give the crude title compound, which was purified by column chromatography (DCM/MeOH, 95:5).

Workup

  1. customThe reaction mixture was irradiated in the microwave reactor at 110° C. for 3 min
  2. extractionThe reaction mixture was extracted with DCM (3×20 ml)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-41fe1de1f3e84bf0a6b4471a6e9e645b
Source dataset
uspto-grants-2014_04
Patent number
US08697723B2

Reaction notes

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