Potassium Carbonate → HCID 69352678, compound

HRID 1609808Notes

Reaction equation

HRID 1609808 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C@H:7]2[CH2:12][CH2:11][CH2:10][NH:9][CH2:8]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:22][C:23]1[CH:31]=[CH:30][C:26]2[O:27][CH2:28][O:29][C:25]=2[CH:24]=1>CN(C=O)C.C(OCC)(=O)C.N[C@H](C(O)=O)CC1C=C2C(C=CC=C2)=CC=1>[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][C@H:7]2[CH2:12][CH2:11][CH2:10][N:9]([CH2:22][C:23]3[CH:31]=[CH:30][C:26]4[O:27][CH2:28][O:29][C:25]=4[CH:24]=3)[CH2:8]2)=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 69351642HCID 69351642, compound

Product 1

HCID 69352678HCID 69352678, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 1859152-NaphthylalanineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To an ice water-cooled solution of (3S)-3-(4-aminophenoxy)piperidine (3.5 g) in DMF (20 mL) was added K2CO3 (7.5 g) and Nal (0.2 g), followed by the addition of 5-chloromethyl-1,3-benzodioxole (4.7 mL). The resulting reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was diluted with ethyl acetate (200 mL), washed with water (100 mL×3) and brine (100 mL), and dried (Na2SO4). The crude product was further purified by column chromatography (methanol:ethyl acetate1:10), to afford (3S)-3-(4-aminophenoxy)-1-[(1,3-benzodioxol-5-yl)methyl]piperidine (4.4 g, 74% yield) as an oil.

Workup

  1. customThe resulting reaction mixture
  2. washwashed with water (100 mL×3) and brine (100 mL)
  3. dry with materialdried (Na2SO4)
  4. customThe crude product was further purified by column chromatography (methanol:ethyl acetate1:10)

Sources & evidence

ORD record
ord-7747ad3d5b4a43fd866ad0def5badcd2
Source dataset
uspto-grants-2006_01
Patent number
US06982259B2

Reaction notes

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