Hydrochloric Acid → HCID 59255443, compound

HRID 77999Notes

Reaction equation

HRID 77999 reaction equation
CO.[O:3]1CCO[CH:4]1[C:8]1[CH:21]=[CH:20][C:11]([CH2:12][NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[C:14]1([NH:13][CH2:12][C:11]2[CH:10]=[CH:9][C:8]([CH:4]=[O:3])=[CH:21][CH:20]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 516892Sodium BicarbonateHCID 59255424(4-[1,3]Dioxolane-2-yl-benzyl)-phenyl-amine

Product 1

HCID 59255443HCID 59255443, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture solution of methanol and tetrahydrofuran (1:1, 20 mL) of (4-[1,3] dioxolane-2-yl-benzyl)-phenyl-amine (4.16 g, 16.3 mmol) described in Manufacturing Example 73-1-2 was added 5N hydrochloric acid (20 mL). This mixture was stirred for 1 hour at room temperature. This mixture was neutralized with saturated aqueous sodium hydrogencarbonate solution, and extracted with ethyl acetate. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (3.5 g). This compound was used in the subsequent reaction without being purified.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-9cddf7124eeb4014a4269d8300fdb9e0
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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