Hydrochloric Acid → 4-(1'-Methanesulfonyl-1',2',3',6'-tetrahydro-[2,4']bipyridinyl-5-yloxymethyl)-piperidine

HRID 222584

Reaction equation

HRID 222584 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH2:23][CH2:24][N:25]([S:28]([CH3:31])(=[O:30])=[O:29])[CH2:26][CH:27]=3)=[N:20][CH:21]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.[OH-].[Na+]>ClCCl>[CH3:31][S:28]([N:25]1[CH2:24][CH:23]=[C:22]([C:19]2[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:21][N:20]=2)[CH2:27][CH2:26]1)(=[O:29])=[O:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 66865062HCID 66865062, compound

Product 1

HCID 668648374-(1'-Methanesulfonyl-1',2',3',6'-tetrahydro-[2,4']bipyridinyl-5-yloxymethyl)-piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a 3-necked flask with a mechanical stirrer is added 4-(1′-methanesulfonyl-1′,2′,3′,6′-tetrahydro-[2,4′]bipyridinyl-5-yloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester (407 g, 0.90 mol) and 6N aq hydrogen chloride (2000 mL, 12.0 mol) is added dropwise at 25° C. The mixture is stirred mechanically at 25° C. for 0.5 h. 1000 mL of dichloromethane are added at 25° C. and the mixture is stirred for 20˜30 min. Layers are separated and aqueous NaOH (1500 mL, 11.6 mol) is added dropwise to the aqueous solution to pH=9˜10 at 25° C. 3200 mL of dichloromethane are added and the mixture is stirred at 25˜30° C. for 40 min. Aqueous solution of NaOH (300 mL, 2.3 mol) is added dropwise to pH >14, until complete dissolution of the solid, the solution is stirred for 20 to 30 min and layers are separated. The aqueous layer is extracted with 1700 mL of dichloromethane. The combined organic layers are washed with 900 mL of water and concentrated. The residue is used for the next step without further purification.

Workup

  1. additionis added dropwise at 25° C
  2. stirringthe mixture is stirred for 20˜30 min
  3. customLayers are separated
  4. stirringthe mixture is stirred at 25˜30° C. for 40 min
  5. stirringthe solution is stirred for 20 to 30 min
  6. customlayers are separated
  7. extractionThe aqueous layer is extracted with 1700 mL of dichloromethane
  8. washThe combined organic layers are washed with 900 mL of water
  9. concentrationconcentrated
  10. customThe residue is used for the next step without further purification

Sources & evidence

ORD record
ord-39c58a5e61744d7f99432862fc89d704
Source dataset
uspto-grants-2012_06
Patent number
US08207344B2

Linked notes

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