Isopropylamine → Dichloroisoproterenol

HRID 1057976Notes

Reaction equation

HRID 1057976 reaction equation
Br[CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1)[OH:4].[CH:13]([NH2:16])([CH3:15])[CH3:14]>CCOC(C)=O>[CH:13]([NH:16][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1)[OH:4])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 3441362-Bromo-1-(3,4-dichlorophenyl)ethanol

Product 1

HCID 5806Dichloroisoproterenol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3.9 g (14 mmol) 2-bromo-1-(3,4-dichlorophenyl)ethanol and 10 ml isopropylamine was sealed and heated to 80° C. for 16 h, then cooled to room temperature, diluted with 500 mL EtOAc, washed with 400 mL saturated aqueous NaHCO3, and 500 mL brine, then dried over Na2SO4, filtered and concentrated. Purification by flash chromatography (5×8 cm silica gel, elute with 250 mL 3%MeOH/CH2Cl2, 100 mL 50% EtOH/CH2Cl2, then 200 mL EtOH) afforded 2.7 g 2-isopropylamino-1-(3,4-dichlorophenyl)ethanol. 1H NMR(400 mHz, CDCl3) 7.48 (d, 1H, J=1.92 Hz); 7.40 (d, 1H, J=8.22 Hz); 7.20 (dd, 1H, J=8.23and 1.92 Hz); 4.59 (dd, 1H, J=8.96 and 3.75 Hz); 2.94 (dd, 1H, J=12.2 and 3.66 Hz); 2.83 (sept, 1H, J=6.31 Hz); 2.57 (dd, 1H, J=12.3 and 8.87 Hz); 1.09 (d, 3H, J=6.31 Hz); 1.08 (d, 3H, J=6.22 Hz).

Workup

  1. customwas sealed
  2. temperaturecooled to room temperature
  3. washwashed with 400 mL saturated aqueous NaHCO3, and 500 mL brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography (5×8 cm silica gel
  8. washelute with 250 mL 3%MeOH/CH2Cl2, 100 mL 50% EtOH/CH2Cl2

Sources & evidence

ORD record
ord-3ff960b7db694635a479f949ddb5a2f2
Source dataset
uspto-grants-2003_02
Patent number
US06515023B2

Reaction notes

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