Diisopropylethylamine → HCID 11486936, compound

HRID 988900Notes

Reaction equation

HRID 988900 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([I:9])[CH:3]=1.[CH:10]1[CH:15]=[CH:14][C:13]([CH:16](Br)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:12][CH:11]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:16]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][C:4]=1[I:9])([C:13]1[CH:14]=[CH:15][CH:10]=[CH:11][CH:12]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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 a-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 (3x) 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 (3x) and brine
  4. dry with materialdried over MgSO4
  5. customPurification on SiO2 column chromoatography (hexanes to 5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-debbcd2f8bf344be9e4b4574e5d2df0b
Source dataset
uspto-grants-2003_10
Patent number
US06635771B2

Reaction notes

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