2-Bromoethanol → HCID 66747597, compound

HRID 1422708Notes

Reaction equation

HRID 1422708 reaction equation
Br[CH2:2][CH2:3][OH:4].[O:5]1[C:10]2[CH:11]=[CH:12][C:13]([CH2:15][N:16]([CH3:23])[CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:14][C:9]=2[O:8][CH2:7][CH2:6]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[O:5]1[C:10]2[CH:11]=[CH:12][C:13]([CH2:15][N:16]([CH3:23])[C:17]3([CH2:2][CH2:3][OH:4])[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]3)=[CH:14][C:9]=2[O:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 66746279HCID 66746279, compound

Product 1

HCID 66747597HCID 66747597, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-ethanol (36 μL, 0.51 mmol, 1.0 eq) is added at room temperature to a stirred solution of (2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-methyl-piperidin-4-yl-amine (148 mg, 0.51 mmol, 1.0 eq) in N,N-dimethylformamide (4 mL), followed by potassium carbonate (70 mg, 0.51 mmol, 1.0 eq). After 15 hours stirring at room temperature, solvent is evaporated and the residue is extracted with ethyl acetate (3×8 mL) and water (8 mL). pH of the aqueous layer is neutralized with a 0.1 N hydrochloric acid aqueous solution. The combined organic layers are dried over sodium sulfate, filtered and concentrated to afford 2-{4-[(2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-methyl-amino]-piperidin-4-yl}-ethanol as a yellow semisolid (160 mg, 93% yield).

Workup

  1. customsolvent is evaporated
  2. extractionthe residue is extracted with ethyl acetate (3×8 mL) and water (8 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-480ecc3c5ac74a2499b5cefbe332d579
Source dataset
uspto-grants-2015_01
Patent number
US08927542B2

Reaction notes

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