Diisopropylethylamine → HCID 11486936, compound

HRID 1008632Notes

Reaction equation

HRID 1008632 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([I:9])[CH:3]=1.Br[CH:11]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:11]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][C:4]=1[I:9])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 236603BromodiphenylmethaneHCID 27576154-Chloro-2-iodoaniline

Product 1

HCID 11486936HCID 11486936, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 4-chloro-2-iodoaniline (16.5 g, 65.1 mmol) in DMF (250 mL) at rt were added □-bromodiphenylmethane (21.5 g, 84.6 mmol) and iPr2NEt (23 mL, 130 mmol) and the reaction mixture was heated at 45° C. overnight. After the volatile was removed under reduced pressure, the residue was dissolved in EtOAc, washed with water (3×) and brine and dried over MgSO4. Purification on SiO2 column chromoatography (hexanes to 5% EtOAc/hexanes) gave the desired Benzhydryl-(4-chloro-2-iodo-phenyl)-amine (26.1 g, 97% yield) as a yellowish solid.

Workup

  1. customAfter the volatile was removed under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with water (3×) and brine
  4. dry with materialdried over MgSO4
  5. customPurification on SiO2 column chromoatography (hexanes to 5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-c6817f6109544cf09ab25c70acbdbef9
Source dataset
uspto-grants-2004_09
Patent number
US06797708B2

Reaction notes

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