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

HRID 453773
Notes
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Reaction equation

HRID 453773 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228
Dimethylformamide
Solvent

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-5417456f581d4388a14f61f275015e65
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492549B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes