Methanol → 3-dipropylamino-5-chloroformylchroman-HCL

HRID 1684064Notes

Reaction equation

HRID 1684064 reaction equation
[CH2:1]([N:4]([CH2:17][CH2:18][CH3:19])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2OC)O[CH2:6]1)[CH2:2][CH3:3].[OH-:20].[Na+].O=S(Cl)[Cl:24].[CH3:26][OH:27]>O>[ClH:24].[CH2:1]([N:4]([CH2:17][CH2:18][CH3:19])[CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:26]([Cl:24])=[O:27])[O:20][CH2:6]1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 30825975-Methoxy-N,N-dipropyl-3,4-dihydro-2H-1-benzopyran-3-amine

Product 1

HCID 190280833-dipropylamino-5-chloroformylchroman-HCL

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Dipropylamino-5-methyloxychroman (Example 2; 400 mg, 1.37 mmol) was dissolved in 10 ml methanol and NaOH (60 mg, 1.5 mmol) in 2 mL H2O was added. The mixture was refluxed for 5 hours, cooled, filtered through Celite and evaporated to dryness. The residue was refluxed in SOCl2 (5 mL, 68 mmol) for 30 minutes. The excess SOCl2 was then removed in vacuo to give 3-dipropylamino-5- chloroformylchroman-HCL as a gum. The pale brown gum was dissolved in CH2Cl2 (50 mL), and a stream of NH3 (g) was introduced during 2 minutes. The solution was washed with aqueous NaHCO3, dried with Na2SO4 and evaporated to dryness. The oil was purified by flash chromatography (silica gel) by elution with ethyl acetate/hexane 1:4.

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. temperaturecooled
  3. filtrationfiltered through Celite
  4. customevaporated to dryness
  5. customThe excess SOCl2 was then removed in vacuo

Sources & evidence

ORD record
ord-e6fd23ec0c2e425c8d42339c68a619d4
Source dataset
uspto-grants-1997_06
Patent number
US05639772

Reaction notes

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