Hydrochloric Acid → (S)-3-(4-piperazin-1-ylmethyl-phenyl)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine

HRID 1841979Notes

Reaction equation

HRID 1841979 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C@@H:21]3[O:30][C:25]4=[N:26][CH:27]=[CH:28][CH:29]=[C:24]4[O:23][CH2:22]3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[N:11]1([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C@@H:21]3[O:30][C:25]4=[N:26][CH:27]=[CH:28][CH:29]=[C:24]4[O:23][CH2:22]3)=[CH:17][CH:16]=2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10340Sodium CarbonateHCID 866953624-[(S)-4-(2,3-Dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl)-benzyl]-piperazine-1-carboxylic acid tert-butyl ester2×

Product 1

HCID 86695358(S)-3-(4-piperazin-1-ylmethyl-phenyl)-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 4-[(S)-4-(2,3-dihydro-[1,4]dioxino[2,3-b]pyridin-3-yl)-benzyl]-piperazine-1-carboxylic acid tert-butyl ester (prepared from Intermediate C and piperazine-1-carboxylic acid tert-butyl ester according to General Method N) (7.32 g, 17.8 mmol) in 1,4-dioxane (200 mL) is added 4M HCl in 1,4-dioxane (22.2 mL, 88.9 mmol). The resulting slurry is stirred overnight. The reaction is poured into water (600 mL) and basified with 2M aqueous Na2CO3. The product is extracted with DCM, and the combined extracts washed with brine and dried over Na2SO4 to afford the title compound (S) as an oil that partially crystallizes.

Workup

  1. extractionThe product is extracted with DCM
  2. washthe combined extracts washed with brine
  3. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-4a4943d2ae7f474abe816fdcd40812af
Source dataset
uspto-grants-2015_02
Patent number
US08946203B2

Reaction notes

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